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Search for "primary amides" in Full Text gives 11 result(s) in Beilstein Journal of Organic Chemistry.
Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach
- Dileep Kumar Singh and
- Rajesh Kumar
Beilstein J. Org. Chem. 2023, 19, 928–955, doi:10.3762/bjoc.19.71
- (P2O5) as a catalyst for the conversion of various aliphatic amines, aromatic amines, sulfonamides and primary amides into N-substituted pyrroles (Scheme 5). These pyrroles were synthesized in 46–100% yields by the modified Clauson–Kaas reaction between amines 10 and 2,5-DMTHF (2) in the presence of
Graphical Abstract
Figure 1: Various pyrrole containing molecules.
Scheme 1: Various synthestic protocols for the synthesis of pyrroles.
Figure 2: A tree-diagram showing various conventional and green protocols for Clauson-Kaas pyrrole synthesis.
Scheme 2: A general reaction of Clauson–Kaas pyrrole synthesis and proposed mechanism.
Scheme 3: AcOH-catalyzed synthesis of pyrroles 5 and 7.
Scheme 4: Synthesis of N-substituted pyrroles 9.
Scheme 5: P2O5-catalyzed synthesis of N-substituted pyrroles 11.
Scheme 6: p-Chloropyridine hydrochloride-catalyzed synthesis of pyrroles 13.
Scheme 7: TfOH-catalyzed synthesis of N-sulfonylpyrroles 15, N-sulfonylindole 16, N-sulfonylcarbazole 17.
Scheme 8: Scandium triflate-catalyzed synthesis of N-substituted pyrroles 19.
Scheme 9: MgI2 etherate-catalyzed synthesis and proposed mechanism of N-arylpyrrole derivatives 21.
Scheme 10: Nicotinamide catalyzed synthesis of pyrroles 23.
Scheme 11: ZrOCl2∙8H2O catalyzed synthesis and proposed mechanism of pyrrole derivatives 25.
Scheme 12: AcONa catalyzed synthesis of N-substituted pyrroles 27.
Scheme 13: Squaric acid-catalyzed synthesis and proposed mechanism of N-substituted pyrroles 29.
Figure 3: Reusability of catalyst γ-Fe2O3@SiO2-Sb-IL in six cycles.
Scheme 14: Magnetic nanoparticle-supported antimony catalyst used in the synthesis of N-substituted pyrroles 31...
Scheme 15: Iron(III) chloride-catalyzed synthesis of N-substituted pyrroles 33.
Scheme 16: Copper-catalyzed Clauson–Kaas synthesis and mechanism of pyrroles 35.
Scheme 17: β-CD-SO3H-catalyzed synthesis and proposed mechanism of pyrroles 37.
Figure 4: Recyclability of β-cyclodextrin-SO3H.
Scheme 18: Solvent-free and catalyst-free synthesis and plausible mechanism of N-substituted pyrroles 39.
Scheme 19: Nano-sulfated TiO2-catalyzed synthesis of N-substituted pyrroles 41.
Figure 5: Plausible mechanism for the formation of N-substituted pyrroles catalyzed by nano-sulfated TiO2 cat...
Scheme 20: Copper nitrate-catalyzed Clauson–Kaas synthesis and mechanism of N-substituted pyrroles 43.
Scheme 21: Synthesis of N-substituted pyrroles 45 by using Co catalyst Co/NGr-C@SiO2-L.
Scheme 22: Zinc-catalyzed synthesis of N-arylpyrroles 47.
Scheme 23: Silica sulfuric acid-catalyzed synthesis of pyrrole derivatives 49.
Scheme 24: Bismuth nitrate-catalyzed synthesis of pyrroles 51.
Scheme 25: L-(+)-tartaric acid-choline chloride-catalyzed Clauson–Kaas synthesis and plausible mechanism of py...
Scheme 26: Microwave-assisted synthesis of N-substituted pyrroles 55 in AcOH or water.
Scheme 27: Synthesis of pyrrole derivatives 57 using a nano-organocatalyst.
Figure 6: Nano-ferric supported glutathione organocatalyst.
Scheme 28: Microwave-assisted synthesis of N-substituted pyrroles 59 in water.
Scheme 29: Iodine-catalyzed synthesis and proposed mechanism of pyrroles 61.
Scheme 30: H3PW12O40/SiO2-catalyzed synthesis of N-substituted pyrroles 63.
Scheme 31: Fe3O4@-γ-Fe2O3-SO3H-catalyzed synthesis of pyrroles 65.
Scheme 32: Mn(NO3)2·4H2O-catalyzed synthesis and proposed mechanism of pyrroles 67.
Scheme 33: p-TsOH∙H2O-catalyzed (method 1) and MW-assisted (method 2) synthesis of N-sulfonylpyrroles 69.
Scheme 34: ([hmim][HSO4]-catalyzed Clauson–Kaas synthesis of pyrroles 71.
Scheme 35: Synthesis of N-substituted pyrroles 73 using K-10 montmorillonite catalyst.
Scheme 36: CeCl3∙7H2O-catalyzed Clauson–Kaas synthesis of pyrroles 75.
Scheme 37: Synthesis of N-substituted pyrroles 77 using Bi(NO3)3∙5H2O.
Scheme 38: Oxone-catalyzed synthesis and proposed mechanism of N-substituted pyrroles 79.
When metal-catalyzed C–H functionalization meets visible-light photocatalysis
- Lucas Guillemard and
- Joanna Wencel-Delord
Beilstein J. Org. Chem. 2020, 16, 1754–1804, doi:10.3762/bjoc.16.147
- aromatic coupling partner, including frequently used Weinreb amides or functionalized secondary and primary amides. Regarding the scope of olefin substrates, the reaction tolerated numerous functional groups including acrylates, vinyl silanes or sulfones which was interesting from the post
Graphical Abstract
Figure 1: Concept of dual synergistic catalysis.
Figure 2: Classification of catalytic systems involving two catalysts.
Figure 3: General mechanism for the dual nickel/photoredox catalytic system.
Figure 4: General mechanisms for C–H activation catalysis involving different reoxidation strategies.
Figure 5: Indole synthesis via dual C–H activation/photoredox catalysis.
Figure 6: Proposed mechanism for the indole synthesis via dual catalysis.
Figure 7: Oxidative Heck reaction on arenes via the dual catalysis.
Figure 8: Proposed mechanism for the Heck reaction on arenes via dual catalysis.
Figure 9: Oxidative Heck reaction on phenols via the dual catalysis.
Figure 10: Proposed mechanism for the Heck reaction on phenols via dual catalysis.
Figure 11: Carbazole synthesis via dual C–H activation/photoredox catalysis.
Figure 12: Proposed mechanism for the carbazole synthesis via dual catalysis.
Figure 13: Carbonylation of enamides via the dual C–H activation/photoredox catalysis.
Figure 14: Proposed mechanism for carbonylation of enamides via dual catalysis.
Figure 15: Annulation of benzamides via the dual C–H activation/photoredox catalysis.
Figure 16: Proposed mechanism for the annulation of benzamides via dual catalysis.
Figure 17: Synthesis of indoles via the dual C–H activation/photoredox catalysis.
Figure 18: Proposed mechanism for the indole synthesis via dual catalysis.
Figure 19: General concept of dual catalysis merging C–H activation and photoredox catalysis.
Figure 20: The first example of dual catalysis merging C–H activation and photoredox catalysis.
Figure 21: Proposed mechanism for the C–H arylation with diazonium salts via dual catalysis.
Figure 22: Dual catalysis merging C–H activation/photoredox using diaryliodonium salts.
Figure 23: Direct arylation via the dual catalytic system reported by Xu.
Figure 24: Direct arylation via dual catalytic system reported by Balaraman.
Figure 25: Direct arylation via dual catalytic system reported by Guo.
Figure 26: C(sp3)–H bond arylation via the dual Pd/photoredox catalytic system.
Figure 27: Acetanilide derivatives acylation via the dual C–H activation/photoredox catalysis.
Figure 28: Proposed mechanism for the C–H acylation with α-ketoacids via dual catalysis.
Figure 29: Acylation of azobenzenes via the dual catalysis C–H activation/photoredox.
Figure 30: C2-acylation of indoles via the dual C–H activation/photoredox catalysis.
Figure 31: Proposed mechanism for the C2-acylation of indoles with aldehydes via dual catalysis.
Figure 32: C2-acylation of indoles via the dual C–H activation/photoredox catalysis.
Figure 33: Perfluoroalkylation of arenes via the dual C–H activation/photoredox catalysis.
Figure 34: Proposed mechanism for perfluoroalkylation of arenes via dual catalysis.
Figure 35: Sulfonylation of 1-naphthylamides via the dual C–H activation/photoredox catalysis.
Figure 36: Proposed mechanism for sulfonylation of 1-naphthylamides via dual catalysis.
Figure 37: meta-C–H Alkylation of arenes via visible-light metallaphotocatalysis.
Figure 38: Alternative procedure for meta-C–H alkylation of arenes via metallaphotocatalysis.
Figure 39: Proposed mechanism for meta-C–H alkylation of arenes via metallaphotocatalysis.
Figure 40: C–H borylation of arenes via visible-light metallaphotocatalysis.
Figure 41: Proposed mechanism for C–H borylation of arenes via visible-light metallaphotocatalysis.
Figure 42: Undirected C–H aryl–aryl cross coupling via dual gold/photoredox catalysis.
Figure 43: Proposed mechanism for the undirected C–H aryl–aryl cross-coupling via dual catalysis.
Figure 44: Undirected C–H arylation of (hetero)arenes via dual manganese/photoredox catalysis.
Figure 45: Proposed mechanism for the undirected arylation of (hetero)arenes via dual catalysis.
Figure 46: Photoinduced C–H arylation of azoles via copper catalysis.
Figure 47: Photo-induced C–H chalcogenation of azoles via copper catalysis.
Figure 48: Decarboxylative C–H adamantylation of azoles via dual cobalt/photoredox catalysis.
Figure 49: Proposed mechanism for the C–H adamantylation of azoles via dual catalysis.
Figure 50: General mechanisms for the “classical” (left) and Cu-free variant (right) Sonogoshira reaction.
Figure 51: First example of a dual palladium/photoredox catalysis for Sonogashira-type couplings.
Figure 52: Arylation of terminal alkynes with diazonium salts via dual gold/photoredox catalysis.
Figure 53: Proposed mechanism for the arylation of terminal alkynes via dual catalysis.
Figure 54: C–H Alkylation of alcohols promoted by H-atom transfer (HAT).
Figure 55: Proposed mechanism for the C–H alkylation of alcohols promoted by HAT.
Figure 56: C(sp3)–H arylation of latent nucleophiles promoted by H-atom transfer.
Figure 57: Proposed mechanism for the C(sp3)–H arylation of latent nucleophiles promoted by HAT.
Figure 58: Direct α-arylation of alcohols promoted by H-atom transfer.
Figure 59: Proposed mechanism for the direct α-arylation of alcohols promoted by HAT.
Figure 60: C–H arylation of amines via dual Ni/photoredox catalysis.
Figure 61: Proposed mechanism for the C–H arylation of amines via dual Ni/photoredox catalysis.
Figure 62: C–H functionalization of nucleophiles via excited ketone/nickel dual catalysis.
Figure 63: Proposed mechanism for the C–H functionalization enabled by excited ketones.
Figure 64: Selective sp3–sp3 cross-coupling promoted by H-atom transfer.
Figure 65: Proposed mechanism for the selective sp3–sp3 cross-coupling promoted by HAT.
Figure 66: Direct C(sp3)–H acylation of amines via dual Ni/photoredox catalysis.
Figure 67: Proposed mechanism for the C–H acylation of amines via dual Ni/photoredox catalysis.
Figure 68: C–H hydroalkylation of internal alkynes via dual Ni/photoredox catalysis.
Figure 69: Proposed mechanism for the C–H hydroalkylation of internal alkynes.
Figure 70: Alternative procedure for the C–H hydroalkylation of ynones, ynoates, and ynamides.
Figure 71: Allylic C(sp3)–H activation via dual Ni/photoredox catalysis.
Figure 72: Proposed mechanism for the allylic C(sp3)–H activation via dual Ni/photoredox catalysis.
Figure 73: Asymmetric allylation of aldehydes via dual Cr/photoredox catalysis.
Figure 74: Proposed mechanism for the asymmetric allylation of aldehydes via dual catalysis.
Figure 75: Aldehyde C–H functionalization promoted by H-atom transfer.
Figure 76: Proposed mechanism for the C–H functionalization of aldehydes promoted by HAT.
Figure 77: Direct C–H arylation of strong aliphatic bonds promoted by HAT.
Figure 78: Proposed mechanism for the C–H arylation of strong aliphatic bonds promoted by HAT.
Figure 79: Direct C–H trifluoromethylation of strong aliphatic bonds promoted by HAT.
Figure 80: Proposed mechanism for the C–H trifluoromethylation of strong aliphatic bonds.
Installation of -SO2F groups onto primary amides
- Jing Liu,
- Shi-Meng Wang,
- Njud S. Alharbi and
- Hua-Li Qin
Beilstein J. Org. Chem. 2019, 15, 1907–1912, doi:10.3762/bjoc.15.186
- Sciences, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia 10.3762/bjoc.15.186 Abstract A protocol of SO2F2-mediated installation of sulfonyl fluoride onto primary amides has been developed providing a new portal to sulfur(VI) fluoride exchange (SuFEx) click chemistry. The generated
- molecules contain pharmaceutically important amide and -SO2F moieties for application in the discovery of new therapeutics. Keywords: N-fluorosulfonyl amides; primary amides; sulfuryl fluoride (SO2F2); Introduction Sulfur(VI) fluoride exchange (SuFEx) is a new class of click chemistry developed by
- carboxylic amides (1r–u) were well-tolerated and afforded the target products in 56–90% yields. In addition, alkyl carboxylic amides were also smoothly transformed into the corresponding products (2v–z). However, primary amides bearing an amino group or a phenolic hydroxy group were not successfully
Graphical Abstract
Figure 1: Representative sulfonyl fluoride compounds applied in medicinal chemistry and chemical biology.
Scheme 1: Synthesis background of N-fluorosulfonyl amides and fluorosulfates.
Scheme 2: Screening of the substrate scope of amides. Reaction conditions: a mixture of amides 1 (1.0 mmol), ...
Scheme 3: Amide resonance model and X-ray single crystal structure of 4e (CCDC 1906002).
Scheme 4: The proposed reaction mechanism.
Synthesis of functionalised β-keto amides by aminoacylation/domino fragmentation of β-enamino amides
- Pavel Yanev and
- Plamen Angelov
Beilstein J. Org. Chem. 2018, 14, 2602–2606, doi:10.3762/bjoc.14.238
- enolates is one of the main synthetic approaches towards β-keto amides and has found numerous applications [1][2][3][4][5][6][7][8][9]. However, while the generation of tertiary amide enolates is straightforward, this is not the case with secondary and primary amides. The NH acidity of the latter compounds
Graphical Abstract
Scheme 1: Preparation of α-C-acylated β-enamino amides 3 and 4. Reagents and conditions: 2, NMM, EtOCOCl, CH2...
Scheme 2: Domino fragmentation of 3 to β-keto amides 5 with competing cyclisation to pyrrolin-4-ones 6. Reage...
Scheme 3: Proposed mechanism for the formation of side products 6.
Scheme 4: Proposed mechanism for the formation of the target β-keto amides 5.
Scheme 5: Reactivity of analogues 9, lacking the auxiliary amino group [34].
Scheme 6: Domino fragmentation of compounds 4 (R2 = R3 = H) to N-protected ω-amino-β-keto amides 11.
Scheme 7: Ring–chain tautomerism in compounds 11b,c,f,j (n = 2) and reduction to the corresponding β-hydroxy ...
Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols
- Xinyun Liu,
- Johnny H. Phan,
- Benjamin J. Haugeberg,
- Shrikant S. Londhe and
- Michael D. Clift
Beilstein J. Org. Chem. 2017, 13, 2895–2901, doi:10.3762/bjoc.13.282
- , entries 8−10). Unfortunately, only sulfinamide 6t provided the desired imine 7t (Table 3, entry 10, 22% yield). In all three cases, a significant amount of benzaldehyde was observed, indicating that electron deficient primary amides (such as 6r−t) are either incapable of promoting transimination, or the
Graphical Abstract
Scheme 1: Established methods for the preparation of imines vs this work.
Scheme 2: Proposed catalytic cycle for quinone-catalyzed deformylation.
Scheme 3: Studies of quinone-catalyzed C−C bond cleavage in related substrates.
Scheme 4: Sequential oxidative deformylation/Mukaiyama−Mannich addition using phenylglycinol.
Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds
- Alexey Yu. Dubovtsev,
- Maksim V. Dmitriev,
- Аndrey N. Maslivets and
- Michael Rubin
Beilstein J. Org. Chem. 2017, 13, 2179–2185, doi:10.3762/bjoc.13.218
- attack of the amine moiety on the ester substituent (Scheme 1). Interestingly, it seems that the substitution at the nitrogen atom in structure 1 is very crucial in governing the desired reactivity. Indeed, our previous attempts to expand the substrate scope to include “vinylogous primary amides” 1a
Graphical Abstract
Scheme 1: Spirocyclization of enamines with 5-methoxycarbonyl-1H-pyrrolediones.
Scheme 2: Non-catalyzed spirocyclization of enoles (vinylogous carbonates and carbamates) with 5-methoxycarbo...
Scheme 3: Acid-catalyzed spirocyclization of enoles (vinylogous carboxylates) with 5-alkoxycarbonyl-1H-pyrrol...
Figure 1: ORTEP drawing of compound 12ab (CCDC 1546062) showing 50% probability amplitude displacement ellips...
Scheme 4: Formation of mono-imines and mono-hydrazones of 1,3-cyclohexanediones and tautomeric equilibrium be...
Scheme 5: Spirocyclizations involving non-bulky ketazinones 17 and 5-alkoxycarbonyl-1H-pyrrolediones 9.
Figure 2: ORTEP drawing of compound 21ab (CCDC 1546063) showing 50% probability amplitude displacement ellips...
Figure 3: ORTEP drawing of compound 22a (CCDC 1546065) showing 50% probability amplitude displacement ellipso...
Scheme 6: Spirocyclizations involving bulky ketazinones 22 and 5-alkoxycarbonyl-1H-pyrrolediones 9.
Figure 4: ORTEP drawing of compound 23aa (CCDC 1546064) showing 50% probability amplitude displacement ellips...
Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid
- Kohei Yamada,
- Naoto Kamimura and
- Munetaka Kunishima
Beilstein J. Org. Chem. 2017, 13, 1478–1485, doi:10.3762/bjoc.13.146
- materials, such as α-haloketones and primary amides [8], alkynes and nitriles [9], amines and α,β-unsaturated carbonyl compounds [10], etc. [11] have been reported. However, these reactions are often conducted under harsh reaction conditions and multistep syntheses of the starting materials are needed. ii
Graphical Abstract
Scheme 1: Our strategy for the concise synthesis of 2,4,5-trisubstituted oxazoles.
Scheme 2: Synthesis of DMPOPOP.
Recent advances in copper-catalyzed C–H bond amidation
- Jie-Ping Wan and
- Yanfeng Jing
Beilstein J. Org. Chem. 2015, 11, 2209–2222, doi:10.3762/bjoc.11.240
- catalysis of CuBr and NBS. By simply stirring at rt, 75 or 90 °C, a variety of primary amides and lactams incorporated aldehydes 57 to yield imides 58 with moderate to excellent yield. In addition, the method also displayed sound application in the synthesis of cyclic imides such as N-methylphthalimide (60
Graphical Abstract
Scheme 1: Copper-catalyzed C–H amidation of tertiary amines.
Scheme 2: Copper-catalyzed C–H amidation and sulfonamidation of tertiary amines.
Scheme 3: Copper-catalyzed sulfonamidation of allylic C–H bonds.
Scheme 4: Copper-catalyzed sulfonamidation of benzylic C–H bonds.
Scheme 5: Copper-catalyzed sulfonamidation of C–H bonds adjacent to oxygen.
Scheme 6: Copper-catalyzed amidation and sulfonamidation of inactivated alkyl C–H bonds.
Scheme 7: Copper-catalyzed amidation and sulfonamidation of inactivated alkanes.
Scheme 8: Copper-catalyzed intramolecular C–H amidation for lactam synthesis.
Scheme 9: Copper-catalyzed intramolecular C–H amidation for lactam synthesis.
Scheme 10: Copper-catalyzed amidation/sulfonamidation of aryl C–H bonds.
Scheme 11: C–H amidation of pyridinylbenzenes and indoles.
Scheme 12: Mechanism of the Cu-catalyzed C2-amidation of indoles.
Scheme 13: Copper-catalyzed, 2-phenyl oxazole-assisted C–H amidation of benzamides.
Scheme 14: DG-assisted amidation/imidation of indole and benzene C–H bonds.
Scheme 15: Copper-catalyzed C–H amination/amidation of quinoline N-oxides.
Scheme 16: Copper-catalyzed aldehyde formyl C–H amidation.
Scheme 17: Copper-catalyzed formamide C–H amidation.
Scheme 18: Copper-catalyzed sulfonamidation of vinyl C–H bonds.
Scheme 19: CuCl2-catalyzed amidation/sulfonamidation of alkynyl C–H bonds.
Scheme 20: Cu(OH)2-catalyzed amidation/sulfonamidation of alkynyl C–H bonds.
Scheme 21: Sulfonamidation-based cascade reaction for the synthesis of tetrahydrotriazines.
Scheme 22: Copper-catalyzed cascade reaction for the synthesis of quinazolinones.
Scheme 23: Copper-catalyzed cascade reactions for the synthesis of fused quinazolinones.
Scheme 24: Copper-catalyzed synthesis of quinazolinones via methyl C–H bond amidation.
Scheme 25: Dicumyl peroxide-based cascade synthesis of quinazolinones.
Scheme 26: Copper-catalyzed cascade reactions for the synthesis of indolinones.
Integration of enabling methods for the automated flow preparation of piperazine-2-carboxamide
- Richard J. Ingham,
- Claudio Battilocchio,
- Joel M. Hawkins and
- Steven V. Ley
Beilstein J. Org. Chem. 2014, 10, 641–652, doi:10.3762/bjoc.10.56
- molecule to the substrate with no byproducts: the addition of water for the nitrile hydration, and the addition of hydrogen to the heteroarene for the reduction. Thus, this sequence is ideal for a fully continuous multi-step process. Results and Discussion Nitrile hydration Primary amides can be prepared
Graphical Abstract
Figure 1: Raspberry Pi® (RPi) computer operating in the laboratory, shown here without its protective case. U...
Figure 2: Two step approach to piperazine-2-carboxamide via hydrolysis followed by reduction. (a) Retrosynthe...
Figure 3: Heterogeneous hydration of pyrazine-2-carbonitrile with hydrous zirconia.
Figure 4: FlowIR™ profile for the reactor output after hydration of pyrazine-2-carbonitrile using hydrous zir...
Figure 5: (a) Fluidic setup for the zirconia catalysed hydration of aromatic nitrile. (b) Raspberry Pi® micro...
Figure 6: Flowchart describing the control sequence for operating and monitoring the hydration reaction. The ...
Figure 7: Profile for a 3 hour reaction simulating a long run. The absorbance shown is that at 1685 cm−1, whi...
Figure 8: Reactor setup for optimisation reactions. A multi-position valve (V2) was used for collecting sampl...
Figure 9: Representation of the control sequence for running experiments under a set of conditions. (See Supporting Information File 3 for...
Figure 10: Reduction products of piperazine-2-carboxamide.
Figure 11: (a) In-line reservoir schematic. The liquid level is measured by observation of a plastic float. (b...
Figure 12: Flow set up for the automated machine assisted synthesis of (R,S)-piperidine-2-carboxamide.
Figure 13: Control sequence for the two-step process.
Figure 14: Chart of monitored parameters over a 15 hour reaction. The output from the hydrolysis step is direc...
The chemistry of amine radical cations produced by visible light photoredox catalysis
- Jie Hu,
- Jiang Wang,
- Theresa H. Nguyen and
- Nan Zheng
Beilstein J. Org. Chem. 2013, 9, 1977–2001, doi:10.3762/bjoc.9.234
- ketones failed to provide the desired products. Amides 68 are generally much more difficult to be oxidized than amines. Their reduction potentials range from 1.2–1.5 V (vs SCE) for tertiary amides to 2.0 V (vs SCE) for primary amides [84] which makes them less susceptible to oxidation by the photoexcited
Graphical Abstract
Scheme 1: Amine radical cations’ mode of reactivity.
Scheme 2: Reductive quenching of photoexcited Ru complexes by Et3N.
Scheme 3: Photoredox aza-Henry reaction.
Scheme 4: Formation of iminium ions using BrCCl3 as stoichiometric oxidant.
Scheme 5: Oxidative functionalization of N-aryltetrahydroisoquinolines using Eosin Y.
Scheme 6: Synthetic and mechanistic studies of Eosin Y-catalyzed aza-Henry reaction.
Scheme 7: Oxidative functionalization of N-aryltetrahydroisoquinolines using RB and GO.
Scheme 8: Merging Ru-based photoredox catalysis and Lewis base catalysis for the Mannich reaction.
Scheme 9: Merging Au-based photoredox catalysis and Lewis base catalysis for the Mannich reaction.
Scheme 10: Merging Ru-based photoredox catalysis and Cu-catalyzed alkynylation reaction.
Scheme 11: Merging Ru-based photoredox catalysis and NHC catalysis.
Scheme 12: 1,3-Dipolar cycloaddition of photogenically formed azomethine ylides.
Scheme 13: Plausible mechanism for photoredox 1,3-dipolar cycloaddition.
Scheme 14: Photoredox-catalyzed cascade reaction for the synthesis of fused isoxazolidines.
Scheme 15: Plausible mechanism for the photoredox-catalyzed cascade reaction.
Scheme 16: Photoredox-catalyzed α-arylation of glycine derivatives.
Scheme 17: Photoredox-catalyzed α-arylation of amides.
Scheme 18: Intramolecular interception of iminium ions by sulfonamides.
Scheme 19: Intramolecular interception of iminium ions by alcohols and sulfonamides.
Scheme 20: Intermolecular interception of iminium ions by phosphites.
Scheme 21: Photoredox-catalyzed oxidative phosphonylation by Eosin Y.
Scheme 22: Conjugated addition of α-amino radicals to Michael acceptors.
Scheme 23: Conjugated addition of α-amino radicals to Michael acceptors assisted by a Brønsted acid.
Scheme 24: Conjugated addition of α-amino radicals derived from anilines to Michael acceptors.
Scheme 25: Oxygen switch between two pathways involving α-amino radicals.
Scheme 26: Interception of α-amino radicals by azodicarboxylates.
Scheme 27: α-Arylation of amines.
Scheme 28: Plausible mechanism for α-arylation of amines.
Scheme 29: Photoinduced C–C bond cleavage of tertiary amines.
Scheme 30: Photoredox cleavage of C–C bonds of 1,2-diamines.
Scheme 31: Proposed mechanism photoredox cleavage of C–C bonds.
Scheme 32: Intermolecular [3 + 2] annulation of cyclopropylamines with olefins.
Scheme 33: Proposed mechanism for intermolecular [3 + 2] annulation.
Scheme 34: Photoinduced clevage of N–N bonds of aromatic hydrazines and hydrazides.
EcoScale, a semi- quantitative tool to select an organic preparation based on economical and ecological parameters
- Koen Van Aken,
- Lucjan Strekowski and
- Luc Patiny
Beilstein J. Org. Chem. 2006, 2, No. 3, doi:10.1186/1860-5397-2-3
- claim that this procedure for preparing primary amides starting from aryl halides is better than another procedure which uses hexamethyldisilazane (HMDS). [26] Therefore, the EcoScale for the latter procedure was also calculated to compare the two preparations. The sum of all penalty points is 68 (Table
Graphical Abstract
Scheme 1: Reduction of nitrobenzene to aniline [23]
Scheme 2: Oxidation of benzyl chloride to benzoic acid [24]
Scheme 3: Synthesis of benzamide [25]
Scheme 4: Synthesis of benzamide using HMDS [26]
