Advances in photoredox catalysis
Visible-light photoredox catalysis received increasing attention in the last decade as a powerful strategy enabling unprecedented transformations in organic synthesis. Compared to other catalytic approaches, photoredox catalysis offers the advantage of enabling the activation of organic substrates under mild reaction conditions, while making use of visible-light irradiation as a sustainable source of energy.
In this special issue, we aim to highlight the field of photoredox catalysis by showcasing those aspects that have brought photoredox catalysis to the forefront of R&D. This includes innovative synthetic applications, new catalyst design, metallaphotoredox chemistry and fundamental physical organic chemistry aspects of photoredox catalysis.
- Full Research Paper
- Published 16 Mar 2020
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Figure 1: A part of the industry around monochloroacetic acid.
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Scheme 1: Redox based activation of haloacetic acid.
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Figure 2: Cyclic voltammogram of monochloroacetic acid and ferrocene with 0.1 M [TBA][PF6] in MeCN. The poten...
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Scheme 2: Initial attempts for lactone formation by photoredox catalysis.
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Scheme 3: The photoredox reaction of TEMPO with monochloroacetic acid catalyzed by fac-[Ir(ppy)3].
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Figure 3: EPR spectra measured (black) and simulated (red) based on the structure of the oxidized photoredox ...
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Scheme 4: Two possible acid-assisted, reductive activation pathways of monochloroacetic acid (A–H = acid).
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Figure 4: Reaction mixtures after overnight irradiation of (A) 4-chloro-4-phenylbutanoic acid (3) and fac-[Ir...
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Scheme 5: Substrate scope of styrene derivatives in the photoredox reaction with monochloroacetic acid. Yield...
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Scheme 6: Proposed reaction mechanism.
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Scheme 7: The photoredox formation of 1-(chloromethoxy)-2,2,6,6-tetramethylpiperidine.
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- Full Research Paper
- Published 21 Apr 2020
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Scheme 1: Examples of photocatalytic C–C bond formation by nucleophilic trapping of a reactive THIQ intermedi...
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Figure 1: Kinetic profile for the benzylation of 1 to 3.
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Scheme 2: Benzylation of N-phenyl-THIQ.
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Scheme 3: Benzylation of substituted N-arylTHIQs.
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Scheme 4: Removal of the PMP protecting group.
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Scheme 5: Alkylation of N-phenyl-THIQ derivatives. Conditions: a2 mol % [Ir(dtbbpy)(ppy)2]PF6, DMA, 60 h; b2 ...
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Scheme 6: Proposed mechanism.
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- Published 23 Apr 2020
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Scheme 1: Norrish type I and II dissociations.
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Scheme 2: Proposed radical pair formation after the photolysis of benzaldehyde (8).
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Scheme 3: Aldehydes in the Paterno–Büchi reaction.
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Scheme 4: 2,3-Diazabicyclo[2.2.1]hept-2-ene (DBH).
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Scheme 5: Dissociation pathways of benzaldehyde.
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Scheme 6: Reactions that lead to polarized products detectable by CIDNP.
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Scheme 7: MMA (26), DEABP (27), and Michler’s ketone (28).
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Scheme 8: Radical intermediates of DEABP.
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Scheme 9: Photoinitiated polymerization of monomeric MMA (26) using the quinoxalines 32 and benzaldehyde (8).
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Scheme 10: Acetone (4) and formaldehyde (35) as photografting initiators.
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Scheme 11: Photografting by employing acetaldehyde (36) as the photoinitiator.
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Scheme 12: Proposed photolysis mechanism for aliphatic ketones 44 and formaldehyde (35).
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Scheme 13: Initiator 50, reductant 51, and benzaldehyde derivatives 52–54 for the polymerization of the methac...
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Scheme 14: Proposed mechanism of the photomediated atom transfer radical polymerization employing the benzalde...
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Scheme 15: cis/trans isomerization employing triplet states of photosensitizers.
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Scheme 16: Salicylaldehyde (68) forms an internal hydrogen bond.
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Scheme 17: Olefin isomerization via energy transfer from a carbonyl compound.
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Scheme 18: Mechanistic pathways for the Paterno–Büchi reaction.
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Scheme 19: Isomeric oxetanes formed after photochemical addition of aryl aldehydes to 2-butenes.
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Scheme 20: Rotation of the C3–C4 bond of the biradical intermediate may lead to all four conformations.
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Scheme 21: Photolysis products of benzaldehyde (8) in different solvents. a) In benzene or ethanol. b) In hex-...
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Scheme 22: N-tert-Butylbenzamide formation proceeds via a benzoyl radical.
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Scheme 23: Photochemical pinacol coupling.
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Scheme 24: Photochemical ATRA catalyzed by 4-anisaldehyde (52).
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Scheme 25: Proposed triplet sensitization mechanism of the ATRA reaction in the presence of 4-anisaldehyde (52...
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Scheme 26: Benzaldehyde-mediated photoredox CDC reaction: compatible amides and ethers.
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Scheme 27: Photoredox cross-dehydrogenative coupling (CDC) conditions and proposed reaction mechanism.
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Scheme 28: Optimized conditions for the photoredox merger reaction.
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Scheme 29: Proposed mechanism for the C(sp3)–H alkylation/arylation of ethers.
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Scheme 30: Substrate scope for the photochemical alkylation of ethers.
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Scheme 31: C(sp3)–H Functionalization of N-containing molecules.
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Scheme 32: Substrate scope for the photochemical alkylation of N-containing molecules.
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Scheme 33: Additional products yielded by the photochemical alkylation reaction of N-containing molecules.
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Scheme 34: C(sp3)–H functionalization of thioethers.
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Scheme 35: Proposed mechanism for the C(sp3)–H alkylation/arylation of N-containing molecules and thioethers.
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Scheme 36: Hydroacylation using 4-cyanobenzaldehyde (53) as the photoinitiator.
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Scheme 37: Selectivity for the formation of the α,α-disubstituted aldehydes.
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Scheme 38: Substrate scope for the photochemical addition of aldehydes to Michael acceptors.
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Scheme 39: Proposed mechanism for the hydroacylation of Michael acceptors using 4-cyanobenzaldehyde (53) as th...
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Scheme 40: Catalytic arylation of aromatic aldehydes by aryl bromides in which the reaction product acts as th...
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Scheme 41: Proposed mechanism for the catalytic arylation of benzaldehydes by aryl bromides in which the react...
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Scheme 42: Functionalization of the chiral cyclobutanes 180.
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Scheme 43: Optimized reaction conditions and proposed mechanism for the sulfonylcyanation of cyclobutenes.
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- Letter
- Published 27 Apr 2020
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Figure 1: Reaction setup (FC: flow controller, BPR: back pressure regulator).
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Scheme 1: Photocatalysts A–I screened for the oxidation of citronellol.
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Figure 2: Conversion and transmission at fixed reaction conditions (0.5 N citronellol, 1 mL/min,1 mol % catal...
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Figure 3: Measured transmission spectrum of a 5 mmol/L (1 mol %) solution of TPP (H) in dichloromethane with ...
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Figure 4: Transmission spectra of rose bengal (D) and the emission spectrum of an LED with a maximum at 524 n...
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Figure 5: Transmission spectra of dimethylanthracene (Gb) and emission spectra of LEDs with maxima at 365, 37...
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Figure 6: Transmission spectra of TPP (H) and emission spectra of LEDs with maxima at 407 and 424 nm, respect...
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Scheme 2: Photooxidation of alpha-terpinene.
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Figure 7: Conversion of alpha-terpinene using the wavelength-adapted TPP (H) concentrations.
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Figure 8: Conversion of alpha-terpinene at different TPP (H) concentrations.
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Figure 9: Conversion of alpha-terpinene (0.5 N) as a function of the wavelength using DMA (Gb) as the catalys...
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Figure 10: Conversion of citronellol at different concentrations of rose bengal (D).
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Figure 11: Conversion of citronellol as a function of the light power (0.5 mol/L of citronellol, 1.34 mmol/L r...
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Figure 12: Absolute conversion of various concentrations of alpha-terpinene at 407 nm using 0.32 mmol/L of TPP...
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- Review
- Published 06 May 2020
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Figure 1: Chemical structures of the porphyrinoids and their absorption spectra: in bold are highlighted the ...
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Figure 2: Photophysical and photochemical processes (Por = porphyrin). Adapted from [12,18].
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Figure 3: Main dual photocatalysts and their oxidative/reductive excited state potentials, including porphyri...
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Scheme 1: Photoredox alkylation of aldehydes with diazo acetates using porphyrins and a Ru complex. aUsing a ...
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Scheme 2: Proposed mechanism for the alkylation of aldehydes with diazo acetates in the presence of TPP.
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Scheme 3: Arylation of heteroarenes with aryldiazonium salts using TPFPP as photocatalyst, and corresponding ...
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Scheme 4: A) Scope with different aryldiazonium salts and enol acetates. B) Photocatalytic cycles and compari...
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Scheme 5: Photoarylation of isopropenyl acetate A) Comparison between batch and continuous-flow approaches an...
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Scheme 6: Dehalogenation induced by red light using thiaporphyrin (STPP).
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Scheme 7: Applications of NiTPP as both photoreductant and photooxidant.
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Scheme 8: Proposed mechanism for obtaining tetrahydroquinolines by reductive quenching.
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Scheme 9: Selenylation and thiolation of anilines.
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Scheme 10: NiTPP as photoredox catalyst in oxidative and reductive quenching, in comparison with other photoca...
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Scheme 11: C–O bond cleavage of 1-phenylethanol using a cobalt porphyrin (CoTMPP) under visible light.
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Scheme 12: Hydration of terminal alkynes by RhIII(TSPP) under visible light irradiation.
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Scheme 13: Regioselective photocatalytic hydro-defluorination of perfluoroarenes by RhIII(TSPP).
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Scheme 14: Formation of 2-methyl-2,3-dihydrobenzofuran by intramolecular hydro-functionalization of allylpheno...
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Scheme 15: Photocatalytic oxidative hydroxylation of arylboronic acids using UNLPF-12 as heterogeneous photoca...
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Scheme 16: Photocatalytic oxidative hydroxylation of arylboronic acids using MOF-525 as heterogeneous photocat...
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Scheme 17: Preparation of the heterogeneous photocatalyst CNH.
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Scheme 18: Photoinduced sulfonation of alkenes with sulfinic acid using CNH as photocatalyst.
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Scheme 19: Sulfonic acid scope of the sulfonation reactions.
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Scheme 20: Regioselective sulfonation reaction of arimistane.
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Scheme 21: Synthesis of quinazolin-4-(3H)-ones.
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Scheme 22: Selective photooxidation of aromatic benzyl alcohols to benzaldehydes using Pt/PCN-224(Zn).
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Scheme 23: Photooxidation of benzaldehydes to benzoic acids using Pt or Pd porphyrins.
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Scheme 24: Photocatalytic reduction of various nitroaromatics using a Ni-MOF.
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Scheme 25: Photoinduced cycloadditions of CO2 with epoxides by MOF1.
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Figure 4: Electronic configurations of the species of oxygen. Adapted from [66].
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Scheme 26: TPP-photocatalyzed generation of 1O2 and its application in organic synthesis. Adapted from [67-69].
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Scheme 27: Pericyclic reactions involving singlet oxygen and their mechanisms. Adapted from [67].
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Scheme 28: First scaled up ascaridole preparation from α-terpinene.
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Scheme 29: Antimalarial drug synthesis using an endoperoxidation approach.
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Scheme 30: Photooxygenation of colchicine.
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Scheme 31: Synthesis of (−)-pinocarvone from abundant (+)-α-pinene.
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Scheme 32: Seeberger’s semi-synthesis of artemisinin.
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Scheme 33: Synthesis of artemisinin using TPP and supercritical CO2.
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Scheme 34: Synthesis of artemisinin using chlorophyll a.
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Scheme 35: Quercitol stereoisomer preparation.
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Scheme 36: Photocatalyzed preparation of naphthoquinones.
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Scheme 37: Continuous endoperoxidation of conjugated dienes and subsequent rearrangements leading to oxidized ...
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Scheme 38: The Opatz group total synthesis of (–)-oxycodone.
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Scheme 39: Biomimetic syntheses of rhodonoids A, B, E, and F.
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Scheme 40: α-Photooxygenation of chiral aldehydes.
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Scheme 41: Asymmetric photooxidation of indanone β-keto esters by singlet oxygen using PTC as a chiral inducer...
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Scheme 42: Asymmetric photooxidation of both β-keto esters and β-keto amides by singlet oxygen using PTC-2 as ...
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Scheme 43: Bifunctional photo-organocatalyst used for the asymmetric oxidation of β-keto esters and β-keto ami...
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Scheme 44: Mechanism of singlet oxygen oxidation of sulfides to sulfoxides.
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Scheme 45: Controlled oxidation of sulfides to sulfoxides using protonated porphyrins as photocatalysts. aIsol...
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Scheme 46: Photochemical oxidation of sulfides to sulfoxides using PdTPFPP as photocatalyst.
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Scheme 47: Controlled oxidation of sulfides to sulfoxides using SnPor@PAF as a photosensitizer.
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Scheme 48: Syntheses of 2D-PdPor-COF and 3D-Pd-COF.
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Scheme 49: Photocatalytic oxidation of A) thioanisole to methyl phenyl sulfoxide and B) various aryl sulfides,...
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Scheme 50: General mechanism for oxidation of amines to imines.
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Scheme 51: Oxidation of secondary amines to imines.
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Scheme 52: Oxidation of secondary amines using Pd-TPFPP as photocatalyst.
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Scheme 53: Oxidative amine coupling using UNLPF-12 as heterogeneous photocatalyst.
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Scheme 54: Synthesis of Por-COF-1 and Por-COF-2.
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Scheme 55: Photocatalytic oxidation of amines to imines by Por-COF-2.
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Scheme 56: Photocyanation of primary amines.
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Scheme 57: Synthesis of ᴅ,ʟ-tert-leucine hydrochloride.
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Scheme 58: Photocyanation of catharanthine and 16-O-acetylvindoline using TPP.
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Scheme 59: Photochemical α-functionalization of N-aryltetrahydroisoquinolines using Pd-TPFPP as photocatalyst.
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Scheme 60: Ugi-type reaction with 1,2,3,4-tetrahydroisoquinoline using molecular oxygen and TPP.
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Scheme 61: Ugi-type reaction with dibenzylamines using molecular oxygen and TPP.
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Scheme 62: Mannich-type reaction of tertiary amines using PdTPFPP as photocatalyst.
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Scheme 63: Oxidative Mannich reaction using UNLPF-12 as heterogeneous photocatalyst.
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Scheme 64: Transformation of amines to α-cyanoepoxides and the proposed mechanism.
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- Full Research Paper
- Published 12 May 2020
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Scheme 1: One-day workflow for fragment-based library generation. QC: Quality control. MPLC: Medium-pressure ...
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Figure 1: Top: high-power blue LED photoreactors. Bottom, from left to right: photoreactor OFF, ON, and ON th...
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Figure 2: TLC–MS equipment: analysis of 5 reactions in 5 minutes.
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Figure 3: Pre-QC validation by 60 MHz benchtop NMR.
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Scheme 2: Scope of the fragment-based library generation: BCP-amines and azetidines. See Supporting Information File 1 for experimental de...
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Scheme 3: Scope of the fragment-based library generation: pyrrolidines, piperidines and morpholines. See Supporting Information File 1 for...
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- Review
- Published 29 May 2020
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Figure 1: Selected examples of organic dyes. Mes-Acr+: 9-mesityl-10-methylacridinium, DCA: 9,10-dicyanoanthra...
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Scheme 1: Activation modes in photocatalysis.
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Scheme 2: Main strategies for the formation of C(sp3) radicals used in organophotocatalysis.
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Scheme 3: Illustrative example for the photocatalytic oxidative generation of radicals from carboxylic acids:...
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Scheme 4: Illustrative example for the photocatalytic reductive generation of C(sp3) radicals from redoxactiv...
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Figure 2: Common substrates for the photocatalytic oxidative generation of C(sp3) radicals.
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Scheme 5: Illustrative example for the photocatalytic oxidative generation of radicals from dihydropyridines ...
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Scheme 6: Illustrative example for the photocatalytic oxidative generation of C(sp3) radicals from trifluorob...
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Scheme 7: Illustrative example for the photocatalytic reductive generation of C(sp3) radicals from benzylic h...
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Scheme 8: Illustrative example for the photocatalytic generation of C(sp3) radicals via direct HAT: the cross...
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Scheme 9: Illustrative example for the photocatalytic generation of C(sp3) radicals via indirect HAT: the deu...
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Scheme 10: Selected precursors for the generation of aryl radicals using organophotocatalysis.
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Scheme 11: Illustrative example for the photocatalytic reductive generation of aryl radicals from aryl diazoni...
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Scheme 12: Illustrative examples for the photocatalytic reductive generation of aryl radicals from haloarenes:...
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Scheme 13: Illustrative example for the photocatalytic reductive generation of aryl radicals from aryl halides...
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Scheme 14: Illustrative example for the photocatalytic reductive generation of aryl radicals from arylsulfonyl...
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Scheme 15: Illustrative example for the reductive photocatalytic generation of aryl radicals from triaryl sulf...
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Scheme 16: Main strategies towards acyl radicals used in organophotocatalysis.
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Scheme 17: Illustrative example for the decarboxylative photocatalytic generation of acyl radicals from α-keto...
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Scheme 18: Illustrative example for the oxidative photocatalytic generation of acyl radicals from acyl silanes...
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Scheme 19: Illustrative example for the oxidative photocatalytic generation of carbamoyl radicals from 4-carba...
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Scheme 20: Illustrative example of the photocatalytic HAT approach for the generation of acyl radicals from al...
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Scheme 21: General reactivity of a) radical cations; b) radical anions; c) the main strategies towards aryl an...
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Scheme 22: Illustrative example for the oxidative photocatalytic generation of alkene radical cations from alk...
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Scheme 23: Illustrative example for the reductive photocatalytic generation of an alkene radical anion from al...
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Figure 3: Structure of C–X radical anions and their neutral derivatives.
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Scheme 24: Illustrative example for the photocatalytic reduction of imines and the generation of an α-amino C(...
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Scheme 25: Illustrative example for the oxidative photocatalytic generation of aryl radical cations from arene...
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Scheme 26: NCR classifications and generation.
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Scheme 27: Illustrative example for the photocatalytic reductive generation of iminyl radicals from O-aryl oxi...
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Scheme 28: Illustrative example for the photocatalytic oxidative generation of iminyl radicals from α-N-oxy ac...
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Scheme 29: Illustrative example for the photocatalytic oxidative generation of iminyl radicals via an N–H bond...
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Scheme 30: Illustrative example for the photocatalytic oxidative generation of amidyl radicals from Weinreb am...
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Scheme 31: Illustrative example for the photocatalytic reductive generation of amidyl radicals from hydroxylam...
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Scheme 32: Illustrative example for the photocatalytic reductive generation of amidyl radicals from N-aminopyr...
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Scheme 33: Illustrative example for the photocatalytic oxidative generation of amidyl radicals from α-amido-ox...
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Scheme 34: Illustrative example for the photocatalytic oxidative generation of aminium radicals: the N-aryltet...
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Scheme 35: Illustrative example for the photocatalytic oxidative generation of nitrogen-centered radical catio...
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Scheme 36: Illustrative example for the photocatalytic oxidative generation of nitrogen-centered radical catio...
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Scheme 37: Illustrative example for the photocatalytic oxidative generation of hydrazonyl radical from hydrazo...
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Scheme 38: Generation of O-radicals.
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Scheme 39: Illustrative examples for the photocatalytic generation of O-radicals from N-alkoxypyridinium salts...
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Scheme 40: Illustrative examples for the photocatalytic generation of O-radicals from alkyl hydroperoxides: th...
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Scheme 41: Illustrative example for the oxidative photocatalytic generation of thiyl radicals from thiols: the...
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Scheme 42: Main strategies and reagents for the generation of sulfonyl radicals used in organophotocatalysis.
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Scheme 43: Illustrative example for the reductive photocatalytic generation of sulfonyl radicals from arylsulf...
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Scheme 44: Illustrative example of a Cl atom abstraction strategy for the photocatalytic generation of sulfamo...
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Scheme 45: Illustrative example for the oxidative photocatalytic generation of sulfonyl radicals from sulfinic...
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Scheme 46: Illustrative example for the photocatalytic generation of electronically excited triplet states: th...
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Scheme 47: Illustrative example for the photocatalytic generation of electronically excited triplet states: th...
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- Full Research Paper
- Published 15 Jun 2020
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Scheme 1: A) Properties and B) synthesis of CF3O-bearing arenes; C) trifluoromethoxylation using the “second”...
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Scheme 2: Optimization of residence time. 19F NMR yields are reported.
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Scheme 3: Scope of photoredox trifluoromethoxylation in continuous-flow. In case of different products, the m...
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Figure 1: Effect of KH2PO4 – other substrates. a Conditions as for entry 15 (Table 2), 1 h residence time; b conditi...
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- Published 18 Jun 2020
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Scheme 1: Photocatalytic transformations of imines.
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Scheme 2: Substrate scope for the radical cross-couplings. Reaction conditions: 1 (0.3 mmol), under argon atm...
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Scheme 3: Substrate scope for the homocoupling. Reaction conditions: 1 (0.3 mmol), under argon atmosphere, is...
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Scheme 4: Reduction of the imine 1a to the amine 4a.
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Scheme 5: Proposed mechanism.
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- Published 23 Jun 2020
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Scheme 1: [3 + 2] cyclization catalyzed by diaryl disulfide.
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Scheme 2: [3 + 2] cycloaddition catalyzed by disulfide.
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Scheme 3: Disulfide-bridged peptide-catalyzed enantioselective cycloaddition.
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Scheme 4: Disulfide-catalyzed [3 + 2] methylenecyclopentane annulations.
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Scheme 5: Disulfide as a HAT cocatalyst in the [4 + 2] cycloaddition reaction.
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Scheme 6: Proposed mechanism of the [4 + 2] cycloaddition reaction using disulfide as a HAT cocatalyst.
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Scheme 7: Disulfide-catalyzed ring expansion of vinyl spiro epoxides.
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Scheme 8: Disulfide-catalyzed aerobic oxidation of diarylacetylene.
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Scheme 9: Disulfide-catalyzed aerobic photooxidative cleavage of olefins.
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Scheme 10: Disulfide-catalyzed aerobic oxidation of 1,3-dicarbonyl compounds.
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Scheme 11: Proposed mechanism of the disulfide-catalyzed aerobic oxidation of 1,3-dicarbonyl compounds.
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Scheme 12: Disulfide-catalyzed oxidation of allyl alcohols.
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Scheme 13: Disulfide-catalyzed diboration of alkynes.
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Scheme 14: Dehalogenative radical cyclization catalyzed by disulfide.
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Scheme 15: Hydrodifluoroacetamidation of alkenes catalyzed by disulfide.
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Scheme 16: Plausible mechanism of the hydrodifluoroacetamidation of alkenes catalyzed by disulfide.
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Scheme 17: Disulfide-cocatalyzed anti-Markovnikov olefin hydration reactions.
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Scheme 18: Disulfide-catalyzed decarboxylation of carboxylic acids.
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Scheme 19: Proposed mechanism of the disulfide-catalyzed decarboxylation of carboxylic acids.
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Scheme 20: Disulfide-catalyzed decarboxylation of carboxylic acids.
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Scheme 21: Disulfide-catalyzed conversion of maleate esters to fumarates and 5H-furanones.
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Scheme 22: Disulfide-catalyzed isomerization of difluorotriethylsilylethylene.
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Scheme 23: Disulfide-catalyzed isomerization of allyl alcohols to carbonyl compounds.
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Scheme 24: Proposed mechanism for the disulfide-catalyzed isomerization of allyl alcohols to carbonyl compound...
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Scheme 25: Diphenyl disulfide-catalyzed enantioselective synthesis of ophirin B.
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Scheme 26: Disulfide-catalyzed isomerization in the total synthesis of (+)-hitachimycin.
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Scheme 27: Disulfide-catalyzed isomerization in the synthesis of (−)-gloeosporone.
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- Review
- Published 25 Jun 2020
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Figure 1: Bioactive phenanthridine and phenanthridinium derivatives.
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Scheme 1: Synthesis of phenanthrenes by a photo-Pschorr reaction.
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Scheme 2: Synthesis of phenanthrenes by a benzannulation reaction.
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Scheme 3: Photocatalytic cyclization of α-bromochalcones for the synthesis of phenanthrenes.
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Figure 2: Carbon-centered and nitrogen-centered radicals used for the synthesis of phenanthridines.
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Scheme 4: General scheme describing the synthesis of phenanthridines from isocyanides via imidoyl radicals.
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Scheme 5: Synthesis of substituted phenanthridines involving the intermediacy of electrophilic radicals.
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Scheme 6: Photocatalyzed synthesis of 6-β-ketoalkyl phenanthridines.
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Scheme 7: Synthesis of 6-substituted phenanthridines through the addition of trifluoromethyl (path a), phenyl...
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Scheme 8: Synthesis of 6-(trifluoromethyl)-7,8-dihydrobenzo[k]phenanthridine.
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Scheme 9: Phenanthridine syntheses by using photogenerated radicals formed through a C–H bond homolytic cleav...
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Scheme 10: Trifluoroacetimidoyl chlorides as starting substrates for the synthesis of 6-(trifluoromethyl)phena...
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Scheme 11: Synthesis of phenanthridines via aryl–aryl-bond formation.
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Scheme 12: Oxidative conversion of N-biarylglycine esters to phenanthridine-6-carboxylates.
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Scheme 13: Photocatalytic synthesis of benzo[f]quinolines from 2-heteroaryl-substituted anilines and heteroary...
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Scheme 14: Synthesis of noravicine (14.2a) and nornitidine (14.2b) alkaloids.
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Scheme 15: Gram-scale synthesis of the alkaloid trisphaeridine (15.3).
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Scheme 16: Synthesis of phenanthridines starting from vinyl azides.
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Scheme 17: Synthesis of pyrido[4,3,2-gh]phenanthridines 17.5a–d through the radical trifluoromethylthiolation ...
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Scheme 18: The direct oxidative C–H amidation involving amidyl radicals for the synthesis of phenanthridones.
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- Review
- Published 26 Jun 2020
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Graphical Abstract
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Figure 1: A) Bar chart of the publications per year for the topics “Photocatalysis” (49,662 instances) and “P...
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Figure 2: A) Professor Giacomo Ciamician and Dr. Paolo Silber on their roof laboratory at the University of B...
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Scheme 1: PRC trifluoromethylation of N-methylpyrrole (1) using hazardous gaseous CF3I safely in a flow react...
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Figure 3: A) Unit cells of the three most common crystal structures of TiO2: rutile, brookite, and anatase. R...
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Figure 4: Illustration of the key semiconductor photocatalysis events: 1) A photon with a frequency exceeding...
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Figure 5: Photocatalytic splitting of water by oxygen vacancies on a TiO2(110) surface. Reprinted with permis...
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Figure 6: Proposed adsorption modes of A) benzene, B) chlorobenzene, C) toluene, D) phenol, E) anisole, and F...
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Figure 7: Structures of the sulfonate-containing organic dyes RB5 (3) and MX-5B (4) and the adsorption isothe...
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Figure 8: Idealised triclinic unit cell of a g-C3N4 type polymer, displaying possible hopping transport scena...
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Figure 9: Idealised structure of a perfect g-C3N4 sheet. The central unit highlighted in red represents one t...
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Figure 10: Timeline of the key processes of charge transport following the photoexcitation of g-C3N4, leading ...
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Scheme 2: Photocatalytic bifunctionalisation of heteroarenes using mpg-C3N4, with the selected examples 5 and ...
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Figure 11: A) Structure of four linear conjugated polymer photocatalysts for hydrogen evolution, displaying th...
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Figure 12: Graphical representation of the common methods used to immobilise molecular photocatalysts (PC) ont...
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Figure 13: Wireless light emitter-supported TiO2 (TiO2@WLE) HPCat spheres powered by resonant inductive coupli...
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Figure 14: Graphical representation of zinc–perylene diimide (Zn-PDI) supramolecular assembly photocatalysis v...
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Scheme 3: Upconversion of NIR photons to the UV frequency by NaYF4:Yb,Tm nanocrystals sequentially coated wit...
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Figure 15: Types of reactors employed in heterogeneous photocatalysis in flow. A) Fixed bed reactors and the s...
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Figure 16: Electrochemical potential of common semiconductor, transition metal, and organic dye-based photocat...
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Scheme 4: Possible mechanisms of an immobilised molecular photoredox catalyst by oxidative or reductive quenc...
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Scheme 5: Scheme of the CMB-C3N4 photocatalytic decarboxylative fluorination of aryloxyacetic acids, with the...
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Scheme 6: Scheme of the g-C3N4 photocatalytic desilylative coupling reaction in flow and proposed mechanism [208].
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Scheme 7: Proposed mechanism of the radical cyclisation of unsaturated alkyl 2-bromo-1,3-dicarbonyl compounds...
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Scheme 8: N-alkylation of benzylamine and schematic of the TiO2-coated microfluidic device [213].
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Scheme 9: Proposed mechanism of the Pt@TiO2 photocatalytic deaminitive cyclisation of ʟ-lysine (23) to ʟ-pipe...
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Scheme 10: A) Proposed mechanism for the photocatalytic oxidation of phenylboronic acid (24). B) Photos and SE...
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Scheme 11: Proposed mechanism for the DA-CMP3 photocatalytic aza-Henry reaction performed in a continuous flow...
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Scheme 12: Proposed mechanism for the formation of the cyclic product 32 by TiO2-NC HPCats in a slurry flow re...
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Scheme 13: Reaction scheme for the photocatalytic synthesis of homo and hetero disulfides in flow and scope of...
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Scheme 14: Reaction scheme for the MoOx/TiO2 HPCat oxidation of cyclohexane (34) to benzene. The graph shows t...
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Scheme 15: Proposed mechanism of the TiO2 HPC heteroarene C–H functionalisation via aryl radicals generated fr...
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Scheme 16: Scheme of the oxidative coupling of benzylamines with the HOTT-HATN HPCat and selected examples of ...
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Scheme 17: Photocatalysis oxidation of benzyl alcohol (40) to benzaldehyde (41) in a microflow reactor coated ...
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Figure 17: Mechanisms of Dexter and Forster energy transfer.
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Scheme 18: Continuous flow process for the isomerisation of alkenes with an ionic liquid-immobilised photocata...
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Scheme 19: Singlet oxygen synthetic step in the total synthesis of canataxpropellane [265].
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Scheme 20: Scheme and proposed mechanism of the singlet oxygen photosensitisation by CMP_X HPCats, with the st...
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Scheme 21: Structures of CMP HPCat materials applied by Vilela and co-workers for the singlet oxygen photosens...
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Scheme 22: Polyvinylchloride resin-supported TDCPP photosensitisers applied for singlet oxygen photosensitisat...
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Scheme 23: Structure of the ionically immobilised TPP photosensitiser on amberlyst-15 ion exchange resins (TPP...
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Scheme 24: Photosensitised singlet oxygen oxidation of citronellol (46) in scCO2, with automatic phase separat...
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Scheme 25: Schematic of PS-Est-BDP-Cl2 being applied for singlet oxygen photosensitisation in flow. A) Pseudo-...
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Scheme 26: Reaction scheme of the singlet oxygen oxidation of furoic acid (54) using a 3D-printed microfluidic...
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Figure 18: A) Photocatalytic bactericidal mechanism by ROS oxidative cleavage of membrane lipids (R = H, amino...
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Figure 19: A) Suggested mechanisms for the aqueous pollutant degradation by TiO2 in a slurry flow reactor [284-287]. B)...
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Figure 20: Schematic of the flow system used for the degradation of aqueous oxytetracycline (56) solutions [215]. M...
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Scheme 27: Degradation of a salicylic acid (57) solution by a coupled solar photoelectro-Fenton (SPEF) process...
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Figure 21: A) Schematic flow diagram using the TiO2-coated NETmix microfluidic device for an efficient mass tr...
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- Review
- Published 21 Jul 2020
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Figure 1: Concept of dual synergistic catalysis.
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Figure 2: Classification of catalytic systems involving two catalysts.
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Figure 3: General mechanism for the dual nickel/photoredox catalytic system.
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Figure 4: General mechanisms for C–H activation catalysis involving different reoxidation strategies.
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Figure 5: Indole synthesis via dual C–H activation/photoredox catalysis.
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Figure 6: Proposed mechanism for the indole synthesis via dual catalysis.
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Figure 7: Oxidative Heck reaction on arenes via the dual catalysis.
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Figure 8: Proposed mechanism for the Heck reaction on arenes via dual catalysis.
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Figure 9: Oxidative Heck reaction on phenols via the dual catalysis.
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Figure 10: Proposed mechanism for the Heck reaction on phenols via dual catalysis.
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Figure 11: Carbazole synthesis via dual C–H activation/photoredox catalysis.
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Figure 12: Proposed mechanism for the carbazole synthesis via dual catalysis.
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Figure 13: Carbonylation of enamides via the dual C–H activation/photoredox catalysis.
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Figure 14: Proposed mechanism for carbonylation of enamides via dual catalysis.
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Figure 15: Annulation of benzamides via the dual C–H activation/photoredox catalysis.
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Figure 16: Proposed mechanism for the annulation of benzamides via dual catalysis.
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Figure 17: Synthesis of indoles via the dual C–H activation/photoredox catalysis.
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Figure 18: Proposed mechanism for the indole synthesis via dual catalysis.
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Figure 19: General concept of dual catalysis merging C–H activation and photoredox catalysis.
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Figure 20: The first example of dual catalysis merging C–H activation and photoredox catalysis.
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Figure 21: Proposed mechanism for the C–H arylation with diazonium salts via dual catalysis.
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Figure 22: Dual catalysis merging C–H activation/photoredox using diaryliodonium salts.
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Figure 23: Direct arylation via the dual catalytic system reported by Xu.
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Figure 24: Direct arylation via dual catalytic system reported by Balaraman.
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Figure 25: Direct arylation via dual catalytic system reported by Guo.
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Figure 26: C(sp3)–H bond arylation via the dual Pd/photoredox catalytic system.
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Figure 27: Acetanilide derivatives acylation via the dual C–H activation/photoredox catalysis.
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Figure 28: Proposed mechanism for the C–H acylation with α-ketoacids via dual catalysis.
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Figure 29: Acylation of azobenzenes via the dual catalysis C–H activation/photoredox.
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Figure 30: C2-acylation of indoles via the dual C–H activation/photoredox catalysis.
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Figure 31: Proposed mechanism for the C2-acylation of indoles with aldehydes via dual catalysis.
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Figure 32: C2-acylation of indoles via the dual C–H activation/photoredox catalysis.
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Figure 33: Perfluoroalkylation of arenes via the dual C–H activation/photoredox catalysis.
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Figure 34: Proposed mechanism for perfluoroalkylation of arenes via dual catalysis.
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Figure 35: Sulfonylation of 1-naphthylamides via the dual C–H activation/photoredox catalysis.
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Figure 36: Proposed mechanism for sulfonylation of 1-naphthylamides via dual catalysis.
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Figure 37: meta-C–H Alkylation of arenes via visible-light metallaphotocatalysis.
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Figure 38: Alternative procedure for meta-C–H alkylation of arenes via metallaphotocatalysis.
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Figure 39: Proposed mechanism for meta-C–H alkylation of arenes via metallaphotocatalysis.
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Figure 40: C–H borylation of arenes via visible-light metallaphotocatalysis.
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Figure 41: Proposed mechanism for C–H borylation of arenes via visible-light metallaphotocatalysis.
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Figure 42: Undirected C–H aryl–aryl cross coupling via dual gold/photoredox catalysis.
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Figure 43: Proposed mechanism for the undirected C–H aryl–aryl cross-coupling via dual catalysis.
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Figure 44: Undirected C–H arylation of (hetero)arenes via dual manganese/photoredox catalysis.
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Figure 45: Proposed mechanism for the undirected arylation of (hetero)arenes via dual catalysis.
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Figure 46: Photoinduced C–H arylation of azoles via copper catalysis.
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Figure 47: Photo-induced C–H chalcogenation of azoles via copper catalysis.
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Figure 48: Decarboxylative C–H adamantylation of azoles via dual cobalt/photoredox catalysis.
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Figure 49: Proposed mechanism for the C–H adamantylation of azoles via dual catalysis.
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Figure 50: General mechanisms for the “classical” (left) and Cu-free variant (right) Sonogoshira reaction.
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Figure 51: First example of a dual palladium/photoredox catalysis for Sonogashira-type couplings.
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Figure 52: Arylation of terminal alkynes with diazonium salts via dual gold/photoredox catalysis.
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Figure 53: Proposed mechanism for the arylation of terminal alkynes via dual catalysis.
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Figure 54: C–H Alkylation of alcohols promoted by H-atom transfer (HAT).
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Figure 55: Proposed mechanism for the C–H alkylation of alcohols promoted by HAT.
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Figure 56: C(sp3)–H arylation of latent nucleophiles promoted by H-atom transfer.
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Figure 57: Proposed mechanism for the C(sp3)–H arylation of latent nucleophiles promoted by HAT.
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Figure 58: Direct α-arylation of alcohols promoted by H-atom transfer.
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Figure 59: Proposed mechanism for the direct α-arylation of alcohols promoted by HAT.
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Figure 60: C–H arylation of amines via dual Ni/photoredox catalysis.
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Figure 61: Proposed mechanism for the C–H arylation of amines via dual Ni/photoredox catalysis.
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Figure 62: C–H functionalization of nucleophiles via excited ketone/nickel dual catalysis.
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Figure 63: Proposed mechanism for the C–H functionalization enabled by excited ketones.
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Figure 64: Selective sp3–sp3 cross-coupling promoted by H-atom transfer.
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Figure 65: Proposed mechanism for the selective sp3–sp3 cross-coupling promoted by HAT.
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Figure 66: Direct C(sp3)–H acylation of amines via dual Ni/photoredox catalysis.
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Figure 67: Proposed mechanism for the C–H acylation of amines via dual Ni/photoredox catalysis.
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Figure 68: C–H hydroalkylation of internal alkynes via dual Ni/photoredox catalysis.
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Figure 69: Proposed mechanism for the C–H hydroalkylation of internal alkynes.
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Figure 70: Alternative procedure for the C–H hydroalkylation of ynones, ynoates, and ynamides.
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Figure 71: Allylic C(sp3)–H activation via dual Ni/photoredox catalysis.
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Figure 72: Proposed mechanism for the allylic C(sp3)–H activation via dual Ni/photoredox catalysis.
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Figure 73: Asymmetric allylation of aldehydes via dual Cr/photoredox catalysis.
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Figure 74: Proposed mechanism for the asymmetric allylation of aldehydes via dual catalysis.
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Figure 75: Aldehyde C–H functionalization promoted by H-atom transfer.
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Figure 76: Proposed mechanism for the C–H functionalization of aldehydes promoted by HAT.
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Figure 77: Direct C–H arylation of strong aliphatic bonds promoted by HAT.
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Figure 78: Proposed mechanism for the C–H arylation of strong aliphatic bonds promoted by HAT.
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Figure 79: Direct C–H trifluoromethylation of strong aliphatic bonds promoted by HAT.
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Figure 80: Proposed mechanism for the C–H trifluoromethylation of strong aliphatic bonds.
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- Letter
- Published 12 Aug 2020
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Scheme 1: Electrophilic activation of allenamides.
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Scheme 2: The planned intramolecular radical addition to allenamides generating the conjugated N-acyliminium ...
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Scheme 3: Photoredox Ir-catalyzed intermolecular addition of bromide 18 and aniline 16 to allenamide 15.
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Scheme 4: Reaction scope (a) allenamide; (b) arylamine nucleophile; (c) alcohol nucleophile.
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Scheme 5: (a) Tentative mechanism for the photoredox-catalyzed formation of the conjugated N-acyliminium inte...
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Supp. Info
- Review
- Published 29 Sep 2020
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Scheme 1: Amine/photoredox-catalysed α-alkylation of aldehydes with alkyl bromides bearing electron-withdrawi...
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Scheme 2: Amine/HAT/photoredox-catalysed α-functionalisation of aldehydes using alkenes.
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Scheme 3: Amine/cobalt/photoredox-catalysed α-functionalisation of ketones and THIQs.
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Scheme 4: Amine/photoredox-catalysed α-functionalisation of aldehydes or ketones with imines. (a) Using keton...
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Scheme 5: Bifunctional amine/photoredox-catalysed enantioselective α-functionalisation of aldehydes.
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Scheme 6: Bifunctional amine/photoredox-catalysed α-functionalisation of aldehydes using amine catalysts via ...
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Scheme 7: Amine/photoredox-catalysed RCA of iminium ion intermediates. (a) Synthesis of quaternary stereocent...
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Scheme 8: Bifunctional amine/photoredox-catalysed RCA of enones in a radical chain reaction initiated by an i...
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Scheme 9: Bifunctional amine/photoredox-catalysed RCA reactions of iminium ions with different radical precur...
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Scheme 10: Bifunctional amine/photoredox-catalysed radical cascade reactions between enones and alkenes with a...
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Scheme 11: Amine/photocatalysed photocycloadditions of iminium ion intermediates. (a) External photocatalyst u...
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Scheme 12: Amine/photoredox-catalysed addition of acrolein (94) to iminium ions.
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Scheme 13: Dual NHC/photoredox-catalysed acylation of THIQs.
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Scheme 14: NHC/photocatalysed spirocyclisation via photoisomerisation of an extended Breslow intermediate.
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Scheme 15: CPA/photoredox-catalysed aza-pinacol cyclisation.
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Scheme 16: CPA/photoredox-catalysed Minisci-type reaction between azaarenes and α-amino radicals.
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Scheme 17: CPA/photoredox-catalysed radical additions to azaarenes. (a) α-Amino radical or ketyl radical addit...
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Scheme 18: CPA/photoredox-catalysed reduction of azaarene-derived substrates. (a) Reduction of ketones. (b) Ex...
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Scheme 19: CPA/photoredox-catalysed radical coupling reactions of α-amino radicals with α-carbonyl radicals. (...
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Scheme 20: CPA/photoredox-catalysed Povarov reaction.
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Scheme 21: CPA/photoredox-catalysed reactions with imines. (a) Decarboxylative imine generation followed by Po...
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Scheme 22: Bifunctional CPA/photocatalysed [2 + 2] photocycloadditions.
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Scheme 23: PTC/photocatalysed oxygenation of 1-indanone-derived β-keto esters.
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Scheme 24: PTC/photoredox-catalysed perfluoroalkylation of 1-indanone-derived β-keto esters via a radical chai...
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Scheme 25: Bifunctional hydrogen bonding/photocatalysed intramolecular [2 + 2] photocycloadditions of quinolon...
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Scheme 26: Bifunctional hydrogen bonding/photocatalysed intramolecular RCA cyclisation of a quinolone.
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Scheme 27: Bifunctional hydrogen bonding/photocatalysed intramolecular [2 + 2] photocycloadditions of quinolon...
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Scheme 28: Bifunctional hydrogen bonding/photocatalysed [2 + 2] photocycloaddition reactions. (a) First use of...
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Scheme 29: Bifunctional hydrogen bonding/photocatalysed deracemisation of allenes.
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Scheme 30: Bifunctional hydrogen bonding/photocatalysed deracemisation reactions. (a) Deracemisation of sulfox...
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Scheme 31: Bifunctional hydrogen bonding/photocatalysed intramolecular [2 + 2] photocycloaddition of coumarins....
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Scheme 32: Bifunctional hydrogen bonding/photocatalysed [2 + 2] photocycloadditions of quinolones. (a) Intramo...
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Scheme 33: Hydrogen bonding/photocatalysed formal arylation of benzofuranones.
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Scheme 34: Hydrogen bonding/photoredox-catalysed dehalogenative protonation of α,α-chlorofluoro ketones.
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Scheme 35: Hydrogen bonding/photoredox-catalysed reductions. (a) Reduction of 1,2-diketones. (b) Reduction of ...
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Scheme 36: Hydrogen bonding/HAT/photocatalysed deracemisation of cyclic ureas.
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Scheme 37: Hydrogen bonding/HAT/photoredox-catalysed synthesis of cyclic sulfonamides.
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Scheme 38: Hydrogen bonding/photoredox-catalysed reaction between imines and indoles.
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Scheme 39: Chiral cation/photoredox-catalysed radical coupling of two α-amino radicals.
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Scheme 40: Chiral phosphate/photoredox-catalysed hydroetherfication of alkenols.
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Scheme 41: Chiral phosphate/photoredox-catalysed synthesis of pyrroloindolines.
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Scheme 42: Chiral anion/photoredox-catalysed radical cation Diels–Alder reaction.
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Scheme 43: Lewis acid/photoredox-catalysed cycloadditions of carbonyls. (a) Formal [2 + 2] cycloaddition of en...
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Scheme 44: Lewis acid/photoredox-catalysed RCA reaction using a scandium Lewis acid between α-amino radicals a...
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Scheme 45: Lewis acid/photoredox-catalysed RCA reaction using a copper Lewis acid between α-amino radicals and...
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Scheme 46: Lewis acid/photoredox-catalysed synthesis of 1,2-amino alcohols from aldehydes and nitrones using a...
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Scheme 47: Lewis acid/photocatalysed [2 + 2] photocycloadditions of enones and alkenes.
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Scheme 48: Meggers’s chiral-at-metal catalysts.
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Scheme 49: Lewis acid/photoredox-catalysed α-functionalisation of ketones with alkyl bromides bearing electron...
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Scheme 50: Bifunctional Lewis acid/photoredox-catalysed radical coupling reaction using α-chloroketones and α-...
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Scheme 51: Lewis acid/photocatalysed RCA of enones. (a) Using aldehydes as acyl radical precursors. (b) Other ...
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Scheme 52: Bifunctional Lewis acid/photocatalysis for a photocycloaddition of enones.
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Scheme 53: Lewis acid/photoredox-catalysed RCA reactions of enones using DHPs as radical precursors.
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Scheme 54: Lewis acid/photoredox-catalysed functionalisation of β-ketoesters. (a) Hydroxylation reaction catal...
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Scheme 55: Bifunctional copper-photocatalysed alkylation of imines.
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Scheme 56: Copper/photocatalysed alkylation of imines. (a) Bifunctional copper catalysis using α-silyl amines....
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Scheme 57: Bifunctional Lewis acid/photocatalysed intramolecular [2 + 2] photocycloaddition.
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Scheme 58: Bifunctional Lewis acid/photocatalysed [2 + 2] photocycloadditions (a) Intramolecular cycloaddition...
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Scheme 59: Bifunctional Lewis acid/photocatalysed rearrangement of 2,4-dieneones.
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Scheme 60: Lewis acid/photocatalysed [2 + 2] cycloadditions of cinnamate esters and styrenes.
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Scheme 61: Nickel/photoredox-catalysed arylation of α-amino acids using aryl bromides.
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Scheme 62: Nickel/photoredox catalysis. (a) Desymmetrisation of cyclic meso-anhydrides using benzyl trifluorob...
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Scheme 63: Nickel/photoredox catalysis for the acyl-carbamoylation of alkenes with aldehydes using TBADT as a ...
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Scheme 64: Bifunctional copper/photoredox-catalysed C–N coupling between α-chloro amides and carbazoles or ind...
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Scheme 65: Bifunctional copper/photoredox-catalysed difunctionalisation of alkenes with alkynes and alkyl or a...
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Scheme 66: Copper/photoredox-catalysed decarboxylative cyanation of benzyl phthalimide esters.
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Scheme 67: Copper/photoredox-catalysed cyanation reactions using TMSCN. (a) Propargylic cyanation (b) Ring ope...
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Scheme 68: Palladium/photoredox-catalysed allylic alkylation reactions. (a) Using alkyl DHPs as radical precur...
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Scheme 69: Manganese/photoredox-catalysed epoxidation of terminal alkenes.
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Scheme 70: Chromium/photoredox-catalysed allylation of aldehydes.
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Scheme 71: Enzyme/photoredox-catalysed dehalogenation of halolactones.
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Scheme 72: Enzyme/photoredox-catalysed dehalogenative cyclisation.
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Scheme 73: Enzyme/photoredox-catalysed reduction of cyclic imines.
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Scheme 74: Enzyme/photocatalysed enantioselective reduction of electron-deficient alkenes as mixtures of (E)/(Z...
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Scheme 75: Enzyme/photoredox catalysis. (a) Deacetoxylation of cyclic ketones. (b) Reduction of heteroaromatic...
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Scheme 76: Enzyme/photoredox-catalysed synthesis of indole-3-ones from 2-arylindoles.
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Scheme 77: Enzyme/HAT/photoredox catalysis for the DKR of primary amines.
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Scheme 78: Bifunctional enzyme/photoredox-catalysed benzylic C–H hydroxylation of trifluoromethylated arenes.
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- Review
- Published 08 Oct 2020
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Figure 1: The momentum transport affects the mass transfer and the light field. All transport phenomena need ...
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Figure 2: Common photomicroreactor designs: (a) Straight channel, (b) serpentine channel, (c) square serpenti...
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Figure 3: Benchmarked photoreactors: (a) Microcapillaries in parallel, (b) microcapillaries in series, (c) fl...
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Figure 4: Photochemical reactions that are detailed in Table 1.
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Figure 5: Structured reactors designed for enhancing the mass transfer: (a) Packed bed photoreactor, (b) mono...
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Figure 6: Comparison of the LED board designs of photomicroreactors: (a) CC array design, (b) MC array design...
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Figure 7: Illustration of the light scattering phenomenon inside a photocatalytic flow reactor.
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Figure 8: Efficiency of the absorption process in scattering situations with respect to pure absorption situa...
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Figure 9: Different types of distributors: (a) Traditional or consecutive manifold, (b) bifurcation unit dist...
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