Search for "polystyrene" in Full Text gives 143 result(s) in Beilstein Journal of Organic Chemistry.
Beilstein J. Org. Chem. 2025, 21, 2604–2611, doi:10.3762/bjoc.21.201
Graphical Abstract
Scheme 1: Synthesis of SG-NHCO-BU1 and SG-BU1 materials based on covalently and non-covalently attached BU1 o...
Figure 1: A) Thermogravimetric analyses of BU1, SG, a-SG, and SG-NHCO-BU1. B) UV–vis titration of K[Au(CN)2] ...
Figure 2: The efficiency of materials (blue SG-BU1, grey SG-NHCO-BU1) in sorbing dicyanoaurate from its water...
Beilstein J. Org. Chem. 2025, 21, 2465–2469, doi:10.3762/bjoc.21.188
Graphical Abstract
Figure 1: Examples of methods for the synthesis of trifluoroacetonitrile and our set-up using a two-chamber r...
Scheme 1: Reactions in chambers A and B. Chamber A: generation of the haloacetonitrile by dehydration of the ...
Figure 2: Glycosyl haloacetimidates synthesized using the two-chamber method.
Figure 3: Synthesis of arylmethylene fluoroacetimidates using the two-chamber method.
Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85
Graphical Abstract
Figure 1: Biologically active cinnamic acid derivatives.
Scheme 1: General synthetic strategies for cinnamic acid derivatizations.
Scheme 2: Cinnamic acid coupling via isobutyl anhydride formation.
Scheme 3: Amidation reaction via O/N-pivaloyl activation.
Scheme 4: Cinnamic acid amidation using TCCA/PPh3 reagent.
Scheme 5: Cinnamic acid amidation using triazine-based reagents.
Scheme 6: Cinnamic acid amidation using continuous flow mechanochemistry.
Scheme 7: Cinnamic acid amidation using COMU as coupling reagent.
Scheme 8: Cinnamic acid amidation using allenone coupling reagent.
Scheme 9: Cinnamic acid amidation using 4-acetamidophenyl triflimide as reagent.
Scheme 10: Cinnamic acid amidation using methyltrimethoxysilane (MTM).
Scheme 11: Cinnamic acid amidation utilizing amine–borane reagent.
Scheme 12: Cinnamic acid amidation using TCCA/PPh3 reagent.
Scheme 13: Cinnamic acid amidation using PPh3/I2 reagent.
Scheme 14: Cinnamic acid amidation using PCl3 reagent.
Scheme 15: Cinnamic acid amidation utilizing pentafluoropyridine (PFP) as reagent.
Scheme 16: Cinnamic acid amidation using hypervalent iodine(III).
Scheme 17: Mechanochemical amidation using 1,1,2,2-tetrafluoroethyl-N,N-dimethylamine (TFEDMA) reagent.
Scheme 18: Methyl ester preparation using tris(2,4,6-trimethoxyphenyl)phosphine (TMPP).
Scheme 19: N-Trifluoromethyl amide preparation using isothiocyanate and AgF.
Scheme 20: POCl3-mediated amide coupling of carboxylic acid and DMF.
Scheme 21: O-Alkylation of cinnamic acid using alkylating agents.
Scheme 22: Glycoside preparation via Mitsunobu reaction.
Scheme 23: O/N-Acylation via rearrangement reactions.
Scheme 24: Amidation reactions using sulfur-based alkylating agents.
Scheme 25: Amidation reaction catalyzed by Pd0 via C–N cleavage.
Scheme 26: Amidation reaction catalyzed by CuCl/PPh3.
Scheme 27: Cu(II) triflate-catalyzed N-difluoroethylimide synthesis.
Scheme 28: Cu/Selectfluor-catalyzed transamidation reaction.
Scheme 29: CuO–CaCO3-catalyzed amidation reaction.
Scheme 30: Ni-catalyzed reductive amidation.
Scheme 31: Lewis acidic transition-metal-catalyzed O/N-acylations.
Scheme 32: Visible-light-promoted amidation of cinnamic acid.
Scheme 33: Sunlight/LED-promoted amidation of cinnamic acid.
Scheme 34: Organophotocatalyst-promoted N–O cleavage of Weinreb amides to synthesize primary amides.
Scheme 35: Cinnamamide synthesis through [Ir] photocatalyst-promoted C–N-bond cleavage of tertiary amines.
Scheme 36: Blue LED-promoted FeCl3-catalyzed reductive transamidation.
Scheme 37: FPyr/TCT-catalyzed amidation of cinnamic acid derivative 121.
Scheme 38: Cs2CO3/DMAP-mediated esterification.
Scheme 39: HBTM organocatalyzed atroposelective N-acylation.
Scheme 40: BH3-catalyzed N-acylation reactions.
Scheme 41: Borane-catalyzed N-acylation reactions.
Scheme 42: Catalytic N-acylation reactions via H/F bonding activation.
Scheme 43: Brønsted base-catalyzed synthesis of cinnamic acid esters.
Scheme 44: DABCO/Fe3O4-catalyzed N-methyl amidation of cinnamic acid 122.
Scheme 45: Catalytic oxidation reactions of acylating agents.
Scheme 46: Preparation of cinnamamide-substituted benzocyclooctene using I(I)/I(III) catalysis.
Scheme 47: Pd-colloids-catalyzed oxidative esterification of cinnamyl alcohol.
Scheme 48: Graphene-supported Pd/Au alloy-catalyzed oxidative esterification via hemiacetal intermediate.
Scheme 49: Au-supported on A) carbon nanotubes (CNT) and B) on porous boron nitride (pBN) as catalyst for the ...
Scheme 50: Cr-based catalyzed oxidative esterification of cinnamyl alcohols with H2O2 as the oxidant.
Scheme 51: Co-based catalysts used for oxidative esterification of cinnamyl alcohol.
Scheme 52: Iron (A) and copper (B)-catalyzed oxidative esterification of cinnamaldehyde.
Scheme 53: NiHPMA-catalyzed oxidative esterification of cinnamaldehyde.
Scheme 54: Synthesis of cinammic acid esters through NHC-catalyzed oxidative esterification via intermolecular...
Scheme 55: Redox-active NHC-catalyzed esterification via intramolecular oxidation.
Scheme 56: Electrochemical conversion of cinnamaldehyde to methyl cinnamate.
Scheme 57: Bu4NI/TBHP-catalyzed synthesis of bisamides from cinnamalaldehyde N-tosylhydrazone.
Scheme 58: Zn/NC-950-catalyzed oxidative esterification of ketone 182.
Scheme 59: Ru-catalyzed oxidative carboxylation of terminal alkenes.
Scheme 60: Direct carboxylation of alkenes using CO2.
Scheme 61: Carboxylation of alkenylboronic acid/ester.
Scheme 62: Carboxylation of gem-difluoroalkenes with CO2.
Scheme 63: Photoredox-catalyzed carboxylation of difluoroalkenes.
Scheme 64: Ru-catalyzed carboxylation of alkenyl halide.
Scheme 65: Carboxylation of alkenyl halides under flow conditions.
Scheme 66: Cinnamic acid ester syntheses through carboxylation of alkenyl sulfides/sulfones.
Scheme 67: Cinnamic acid derivatives synthesis through a Ag-catalyzed decarboxylative cross-coupling proceedin...
Scheme 68: Pd-catalyzed alkyne hydrocarbonylation.
Scheme 69: Fe-catalyzed alkyne hydrocarbonylation.
Scheme 70: Alkyne hydrocarboxylation using CO2.
Scheme 71: Alkyne hydrocarboxylation using HCO2H as CO surrogate.
Scheme 72: Co/AlMe3-catalyzed alkyne hydrocarboxylation using DMF.
Scheme 73: Au-catalyzed oxidation of Au–allenylidenes.
Scheme 74: Pd-catalyzed C–C-bond activation of cyclopropenones to synthesize unsaturated esters and amides.
Scheme 75: Ag-catalyzed C–C-bond activation of diphenylcyclopropenone.
Scheme 76: Cu-catalyzed C–C bond activation of diphenylcyclopropenone.
Scheme 77: PPh3-catalyzed C–C-bond activation of diphenylcyclopropenone.
Scheme 78: Catalyst-free C–C-bond activation of diphenylcyclopropenone.
Scheme 79: Cu-catalyzed dioxolane cleavage.
Scheme 80: Multicomponent coupling reactions.
Scheme 81: Pd-catalyzed partial hydrogenation of electrophilic alkynes.
Scheme 82: Nickel and cobalt as earth-abundant transition metals used as catalysts for the partial hydrogenati...
Scheme 83: Metal-free-catalyzed partial hydrogenation of conjugated alkynes.
Scheme 84: Horner–Wadsworth–Emmons reaction between triethyl 2-fluoro-2-phosphonoacetate and aldehydes with ei...
Scheme 85: Preparation of E/Z-cinnamates using thiouronium ylides.
Scheme 86: Transition-metal-catalyzed ylide reactions.
Scheme 87: Redox-driven ylide reactions.
Scheme 88: Noble transition-metal-catalyzed olefination via carbenoid species.
Scheme 89: TrBF4-catalyzed olefination via carbene species.
Scheme 90: Grubbs catalyst (cat 7)/photocatalyst-mediated metathesis reactions.
Scheme 91: Elemental I2-catalyzed carbonyl-olefin metathesis.
Scheme 92: Cu-photocatalyzed E-to-Z isomerization of cinnamic acid derivatives.
Scheme 93: Ni-catalyzed E-to-Z isomerization.
Scheme 94: Dehydration of β-hydroxy esters via an E1cB mechanism to access (E)-cinnamic acid esters.
Scheme 95: Domino ring-opening reaction induced by a base.
Scheme 96: Dehydroamination of α-aminoester derivatives.
Scheme 97: Accessing methyl cinnamate (44) via metal-free deamination or decarboxylation.
Scheme 98: The core–shell magnetic nanosupport-catalyzed condensation reaction.
Scheme 99: Accessing cinnamic acid derivatives from acetic acid esters/amides through α-olefination.
Scheme 100: Accessing cinnamic acid derivatives via acceptorless α,β-dehydrogenation.
Scheme 101: Cu-catalyzed formal [3 + 2] cycloaddition.
Scheme 102: Pd-catalyzed C–C bond formation via 1,4-Pd-shift.
Scheme 103: NHC-catalyzed Rauhut–Currier reactions.
Scheme 104: Heck-type reaction for Cα arylation.
Scheme 105: Cu-catalyzed trifluoromethylation of cinnamamide.
Scheme 106: Ru-catalyzed alkenylation of arenes using directing groups.
Scheme 107: Earth-abundant transition-metal-catalyzed hydroarylation of α,β-alkynyl ester 374.
Scheme 108: Precious transition-metal-catalyzed β-arylation of cinnamic acid amide/ester.
Scheme 109: Pd-catalyzed β-amination of cinnamamide.
Scheme 110: S8-mediated β-amination of methyl cinnamate (44).
Scheme 111: Pd-catalyzed cross-coupling reaction of alkynyl esters with phenylsilanes.
Scheme 112: Pd-catalyzed β-cyanation of alkynyl amide/ester.
Scheme 113: Au-catalyzed β-amination of alkynyl ester 374.
Scheme 114: Metal-free-catalyzed Cβ-functionalizations of alkynyl esters.
Scheme 115: Heck-type reactions.
Scheme 116: Mizoroki–Heck coupling reactions using unconventional functionalized arenes.
Scheme 117: Functional group-directed Mizoroki–Heck coupling reactions.
Scheme 118: Pd nanoparticles-catalyzed Mizoroki–Heck coupling reactions.
Scheme 119: Catellani-type reactions to access methyl cinnamate with multifunctionalized arene.
Scheme 120: Multicomponent coupling reactions.
Scheme 121: Single atom Pt-catalyzed Heck coupling reaction.
Scheme 122: Earth-abundant transition metal-catalyzed Heck coupling reactions.
Scheme 123: Polymer-coated earth-abundant transition metals-catalyzed Heck coupling reactions.
Scheme 124: Earth-abundant transition-metal-based nanoparticles as catalysts for Heck coupling reactions.
Scheme 125: CN- and Si-based directing groups to access o-selective cinnamic acid derivatives.
Scheme 126: Amide-based directing group to access o-selective cinnamic acid derivatives.
Scheme 127: Carbonyl-based directing group to access o-selective cinnamic acid derivatives.
Scheme 128: Stereoselective preparation of atropisomers via o-selective C(sp2)–H functionalization.
Scheme 129: meta-Selective C(sp2)–H functionalization using directing group-tethered arenes.
Scheme 130: para-Selective C(sp2)–H functionalization using directing group-tethered arenes.
Scheme 131: Non-directed C(sp2)–H functionalization via electrooxidative Fujiwara–Moritani reaction.
Scheme 132: Interconversion of functional groups attached to cinnamic acid.
Scheme 133: meta-Selective C(sp2)–H functionalization of cinnamate ester.
Scheme 134: C(sp2)–F arylation using Grignard reagents.
Scheme 135: Truce–Smiles rearrangement of N-aryl metacrylamides.
Scheme 136: Phosphine-catalyzed cyclization of γ-vinyl allenoate with enamino esters.
Beilstein J. Org. Chem. 2025, 21, 964–998, doi:10.3762/bjoc.21.80
Graphical Abstract
Figure 1: a) Tris(trichlorophenyl)methyl (TTM) radical and related trityl radicals, b) HDMO, SOMO, LUMO orbit...
Figure 2: Mixed halide tri- and perhalogenated triphenylmethyl radicals: a) Molecular structures of homo- and...
Figure 3: Pyridine-functionalized triarylmethyl radicals. a) Chemical structures of X2PyBTM, Py2MTM, and Au-F2...
Figure 4: Pyridine-functionalized triarylmethyl radicals. a) Molecular structure of Mes2F2PyBTM, and b) its f...
Figure 5: Carbazole functionalized triarylmethyl radical. a) Chemical structure of Cz-BTM and b) its energy d...
Figure 6: Donor-functionalized triphenylmethyl radicals. Molecular structures of TTM-Cz, DTM-Cz, TTM-3PCz, PT...
Figure 7: Tuning of the donor strength. Functionalization with electron-donating and electron-withdrawing gro...
Figure 8: Tuning of the donor strength, by varying the Cz-derived donor (1–36) on a TTM radical fragment. a) ...
Figure 9: Three-state model and Marcus theory: q is the charge transfer coordinate and G the free energy. Gro...
Figure 10: Dendronized carbazole donors on TTM radicals. a) Molecular structures of G3TTM and G4TTM. b) Photol...
Figure 11: Electronic extension of the Cz donor. a) Molecular structures and optoelectronic properties of TTM-...
Figure 12: Kekulé diradicals: a) hexadeca- and perchlorinated Thiele (TTH, PTH), Chichibabin (TTM-TTM, PTM-PTM...
Figure 13: Non-Kekulé diradicals: perchlorinated Schlenk–Brauns radical (m-PTH), meta-coupled TTM radicals in ...
Figure 14: UV–vis absorption and photoluminescence spectra of a) TTH in solvents of different polarity, b) dir...
Figure 15: Molecular structures of m-4BTH (meta-butylated Thiele hydrocarbon), m-4TTH (meta-trichlorinated Thi...
Figure 16: a) Polystyrene-based TTM-Cz polymer. b) Molecular structure of radical particles with backbone thro...
Figure 17: Molecular structures of polyradicals. a) Molecular structures of p-TBr6Cl3M-F8, p-TBr6Cl3M-acF8 and ...
Figure 18: Structures of coordination and metal-organic frameworks. a) Carboxylic acid functionalized monomers...
Figure 19: Structures of coordination and metal-organic frameworks. a) Molecular structures of monomers TTMDI, ...
Figure 20: Molecular structures of covalent organic frameworks m-TPM-Ph-COF, m-PTM-Ph-COF, p-TPH-COF, p-PTH-COF...
Figure 21: Molecular structures of covalent organic frameworks PTMAc-COF, oxTAMAc-COF, TOTAc-COF, PTMTAz-COF, p...
Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45
Graphical Abstract
Scheme 1: Features of the ideal reaction (redrawn from P. A. Wender et al. [1]).
Scheme 2: Some of the most popular MCRs with formaldehyde as the carbonyl component.
Scheme 3: Ugi reaction under a catalyzed electro-oxidation process using TEMPO (2,2,6,6-tetramethyl-1-piperid...
Scheme 4: Examples of different products obtained by MCRs in which DMSO serves as -SCH3 source.
Scheme 5: Mechanism of the decomposition of DMSO under acidic or thermal conditions. a) In situ generation of...
Scheme 6: Povarov multicomponent reaction to quinolines.
Scheme 7: Example of the Povarov reaction with formaldehyde with a julolidine derivative as main product.
Scheme 8: Povarov multicomponent reaction to quinoline derivatives I and II using DMSO as formaldehyde surrog...
Scheme 9: Example of a Povarov three-component reaction with change of catalyst, yielding regioisomer III. In...
Scheme 10: The Povarov three-component reactions carried out under acidic catalysis to afford quinoline regios...
Scheme 11: Different MCR routes involving DMSO to synthesize complex heterocycles such as diarylpyridines and ...
Scheme 12: Pyrazole synthesis by a three-component reaction using DMSO as a source of a C-1 unit.
Scheme 13: Three-component reactions for the synthesis of aliphatic heterocycles 13 and 14 using DMSO as a for...
Scheme 14: Proposed mechanism for the 3CR between homoallylic amines, disulfides, and DMSO.
Scheme 15: Mannich-type reaction using DMSO as formaldehyde surrogate.
Scheme 16: Mechanism for the 3CR-Mannich-type reaction between aryl ketone 18, saccharine (19), and DMSO. The ...
Scheme 17: Mannich-type reaction using DMSO as formaldehyde surrogate and under oxidative activation.
Scheme 18: Three-component reaction between an indazole, a carboxylic acid, and DMSO.
Scheme 19: Amine–aldehyde–alkyne (AAA) coupling reaction and plausible mechanism.
Scheme 20: AHA coupling for the synthesis of propargylamines using dihalomethanes as C1 building blocks.
Scheme 21: AHA coupling using CH2Cl2 as both solvent and methylene source.
Scheme 22: Examples of propargylamines synthesized under catalytic AHA protocols.
Scheme 23: Proposed mechanism for the synthesis of propargylamines using dichloromethane as a C1 source.
Scheme 24: Mechanism proposed for the generation of the aminal intermediate E by Buckley et al. [68].
Scheme 25: Pudovic and Kabachnik–Fields reactions for the synthesis of α-aminophosphonates.
Scheme 26: a) Abramov side reaction that generates α-hydroxy phosphonate as a byproduct during the Kabachnik-F...
Scheme 27: Catalyst-free three component reaction to afford α-amino phosphorus product 35 using 1,1-dihaloalka...
Scheme 28: a) Proposed mechanism for the three-component reaction of dichloromethane, amine and phosphorus com...
Scheme 29: Ugi-ammonia strategy using HMTA as a formaldehyde surrogate.
Scheme 30: Glyoxylate and its derivatives as C1 building blocks.
Scheme 31: The Groebke–Blackburn–Bienaymé multicomponent reaction (GBB) and its mechanism.
Scheme 32: a) Byproducts in the GBB multicomponent reaction (GBB) when formaldehyde is used as the carbonyl co...
Scheme 33: Possible regioisomers in the GBB multicomponent reaction when formaldehyde is used as the carbonyl ...
Scheme 34: The multicomponent GBB reaction yields 2-unsubstituted 3-aminoimidazo heterocycles 42a using MP-gly...
Scheme 35: GBB multicomponent reaction to 2-unsubstituted 3-amino imidazo heterocycles 42a using glyoxylic aci...
Scheme 36: GBB reaction using glyoxylic acid immobilized on silica as formaldehyde surrogate.
Scheme 37: Bioactive products synthesized by the GBB reaction using glyoxylic acid.
Scheme 38: van Leusen three-component reaction to imidazoles.
Scheme 39: Side reaction during the synthesis of imidazoles with formaldehyde as the carbonyl compound.
Scheme 40: Optimization of the van Leusen three component reaction to 1,4-disubstituted imidazoles 43 using gl...
Scheme 41: Application of the Sisko strategy [96] for the synthesis of CB1 receptor antagonist compounds [97].
Scheme 42: Side reaction, when NH4OH is used as amine component.
Scheme 43: Ugi-type adducts with the ester moiety and the acidic CH to be used for post-cyclization sequences.
Scheme 44: Ugi/cycloisomerization process to pyrrolones 51, butenolides 52, and pyrroline 53.
Scheme 45: Radical cyclization reactions from Ugi adducts promoted by TEMPO.
Scheme 46: Hydrolysis and decarboxylation reactions to products with incorporation of a C1 unit of ethyl glyox...
Scheme 47: One-step synthetic route to pyrrolones 60 using phenylglyoxal.
Scheme 48: Ugi-pseudo-Knoevenagel-pseudo-Dieckmann cascade sequence for the synthesis of fused heterocycles.
Scheme 49: Ugi-pseudo-Knoevenagel reaction from ethyl glyoxylate.
Beilstein J. Org. Chem. 2025, 21, 47–54, doi:10.3762/bjoc.21.5
Graphical Abstract
Scheme 1: i) Synthesis of benzyl glutamate NCA using phosgene and propylene oxide as a scavenger. ii) Ring-op...
Figure 1: i) The PBLG-PSar block copolymers are dissolved in DMF and then assembled though the solvent-exchan...
Figure 2: Progression of shape transformation of PSar-PBLG vesicles at 70 °C (scalebar 0.5 µm). a) Initial (0...
Figure 3: The temperature-dependent behavior of vesicles and shape Transformation: a) Thermograph of PBLG-PSa...
Beilstein J. Org. Chem. 2025, 21, 10–38, doi:10.3762/bjoc.21.3
Graphical Abstract
Figure 1: A high-level representation of the workflow and framework used for the optimization of organic reac...
Figure 2: (a) Photograph showing a Chemspeed HTE platform using 96-well reaction blocks. (b) Mobile robot equ...
Figure 3: (a) Description of a slug flow platform developed using segments of gas as separation medium for hi...
Figure 4: Schematic representation (a) and photograph (b) of the flow parallel synthesizer intelligently desi...
Figure 5: (a) Schematic representation of an ASFR for obtaining an optimal solution with minimal human interv...
Figure 6: (a) A modular flow platform developed for a wider variety of chemical syntheses. (b) Various catego...
Figure 7: Implementation of four complementary PATs into the optimization process of a three-step synthesis.
Figure 8: Overlay of several Raman spectra of a single condition featuring the styrene vinyl region (a) and t...
Figure 9: (a) Schematic description of the process of chemical reaction optimization through ML methods. (b) ...
Figure 10: (a) Comparison between a standard GP (single-task) and a multitask GP. Training an auxiliary task u...
Figure 11: Comparison of the reaction yield between optimizations campaign where the catalyst ligand selection...
Beilstein J. Org. Chem. 2024, 20, 2493–2499, doi:10.3762/bjoc.20.213
Graphical Abstract
Scheme 1: Strategies for Achmatowicz rearrangement.
Figure 1: Scope of the integrated continuous photo-flow (visible light)-induced Achmatowicz rearrangement rea...
Figure 2: Proposed mechanism for the photochemically induced Achmatowicz rearrangement.
Beilstein J. Org. Chem. 2024, 20, 2129–2142, doi:10.3762/bjoc.20.183
Graphical Abstract
Scheme 1: Esterification of oleic acid (1) with propylsulfonic acid (Pr-SO3H)-functionalised mesoporous silic...
Scheme 2: Using confinement of organocatalytic units for improving the enantioselectivity of silica-supported...
Scheme 3: Michael addition catalysed by cinchona thiourea immobilised on magnetic nanoparticles (13).
Scheme 4: Michael addition catalysed by cinchona thiourea in the presence of magnetic nanoparticles.
Scheme 5: Benzoin condensation catalysed by N-benzylthiazolium salt attached to mesoporous material.
Scheme 6: Photoinduced RAFT polymerisation of n-butyl acrylate (19) catalysed by silica nanoparticle-supporte...
Scheme 7: Pressure and temperature dependence of the 1,4-addition of propanal to trans-β-nitrostyrene under c...
Scheme 8: α-Amination of ethyl 2-oxocyclopentanecarboxylate catalysed by PS-THU which could be recycled over ...
Scheme 9: Preparation of supported catalysts C29–C31 from cinchona squaramides 29–31 modified with a primary ...
Scheme 10: Application of PGMA-supported organocatalysts C29–C31 in the asymmetric Michael addition of pentane...
Scheme 11: Alcoholytic desymmetrisation of a cyclic anhydride 34 catalysed by polyamide-supported cinchona sul...
Beilstein J. Org. Chem. 2024, 20, 2078–2083, doi:10.3762/bjoc.20.179
Graphical Abstract
Scheme 1: Synthesis of cross-linked microgel labelled with aminofluorescein.
Figure 1: Single droplets of the Pickering emulsion attached to a glass surface.
Figure 2: Cage-like microstructure obtained via sequential Ugi reactions.
Figure 3: AFM images of A) single domains and B) cross-linked CMC/chitosan polymer particles.
Figure 4: Variations of microstructures obtained via sequential Ugi reactions. A) Cap-like structures at 5 mo...
Beilstein J. Org. Chem. 2024, 20, 1800–1816, doi:10.3762/bjoc.20.159
Graphical Abstract
Figure 1: Phylogenetic trees of the LanM synthetase amino acid sequences. Unrooted phylogenetic tree of all t...
Figure 2: The phylogenetic tree was built by concatenating 1000 shared clostridial genes (left) between the s...
Figure 3: A. Similarity network created with the ESI web tool with the precursor peptide amino acid sequences...
Figure 4: Mass-spectrometric analysis of purified clostrisin and cellulosin (ESIMS spectra). A1 and A2: CloA2...
Figure 5: Growth curves of the strains with the bacterial activity of the samples. A. Precursor peptide for C...
Figure 6: Atomic force microscopy images (peak force mode) of S. epidermidis MIQ43 incubated with the differe...
Beilstein J. Org. Chem. 2024, 20, 1270–1277, doi:10.3762/bjoc.20.109
Graphical Abstract
Figure 1: Characterization data. (a) FTIR spectra of t-Bu-FIDO and t-Bu-FIDS. (b) UV–vis spectra of fullerene...
Figure 2: Single-crystal structure of t-Bu-FIDS. (a) The π–π distance between two molecules. (b) Crystal pack...
Figure 3: Cyclic voltammograms of fullerene derivatives in o-DCB solution containing Bu4N+(CF3SO2)2N− (0.1 M)...
Figure 4: J–V curves of BHJ OPV devices. (a) ITO/ZnO/fullerene:P3HT (1:1, w/w)/PEDOT:PSS/Ag. (b) ITO/ZnO/full...
Beilstein J. Org. Chem. 2024, 20, 684–691, doi:10.3762/bjoc.20.62
Graphical Abstract
Scheme 1: The preparation of 5-isopropyl-5-methyl-2-(pyridin-2-yl)imidazolidin-4-one derivatives and their ap...
Figure 1: The structure of newly designed ligands I–IV.
Figure 2: Plausible transition structures for the Henry reaction.
Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36
Graphical Abstract
Scheme 1: Examples of BIMs used for their medicinal properties.
Scheme 2: Mechanisms for the synthesis of BIMs using protic or Lewis acids as catalysts.
Scheme 3: Synthesis of bis(indolyl)methanes using DBDMH.
Scheme 4: Competition experiments and synthesis of bis(indolyl)methanes using DBDMH.
Scheme 5: Proposed mechanism for formation of BIM of using DBDMH.
Scheme 6: Synthesis of bis(indolyl)methanes using I2.
Scheme 7: General reaction mechanism upon halogen bonding.
Scheme 8: Synthesis of bis(indolyl)methanes using I2, introduced by Ji.
Scheme 9: Synthesis of bis(indolyl)methanes using Br2 in CH3CN.
Scheme 10: Βidentate halogen-bond donors.
Scheme 11: Synthesis of bis(indolyl)methanes using bidentate halogen-bond donor 26.
Scheme 12: Proposed reaction mechanism.
Scheme 13: Synthesis of bis(indolyl)methanes using iodoalkyne as catalyst.
Scheme 14: Proposed reaction mechanism.
Scheme 15: Optimized reaction conditions used by Ramshini.
Scheme 16: Activation of the carbonyl group by HPA/TPI-Fe3O4.
Scheme 17: Synthesis of BIMs in the presence of nanoAg-Pt/SiO2-doped silicate.
Scheme 18: Mechanism of action proposed by Khalafi-Nezhad et al.
Scheme 19: Activation of the carbonyl group by the Cu–isatin Schiff base complex.
Scheme 20: Optimum reaction conditions published by Jain.
Scheme 21: Organocatalytic protocol utilizing nanoparticles introduced by Bankar.
Scheme 22: Activation of the carbonyl group by the AlCl3·6H2O-SDS-SiO2 complex.
Scheme 23: Optimal reaction conditions for the aforementioned nano-Fe3O4 based catalysts.
Scheme 24: Nanocatalytic protocol proposed by Kaur et al.
Scheme 25: Microwave approach introduced by Yuan.
Scheme 26: Microwave approach introduced by Zahran et al.
Scheme 27: Microwave irradiation protocol introduced by Bindu.
Scheme 28: Silica-supported microwave irradiation protocol.
Scheme 29: Proposed mechanism for formation of BIM by Nongkhlaw.
Scheme 30: Microwave-assisted synthesis of BIMs catalyzed by succinic acid.
Scheme 31: Proposed mechanism of action of MMO-4.
Scheme 32: Catalytic approach introduced by Muhammadpoor-Baltork et al.
Scheme 33: Reaction conditions used by Xiao-Ming.
Scheme 34: Ultrasonic irradiation-based protocol published by Saeednia.
Scheme 35: Pyruvic acid-mediated synthesis of BIMs proposed by Thopate.
Scheme 36: Synthesis of BIMs using [bmim]BF4 or [bmim]PF6 ionic liquids.
Scheme 37: Synthesis of BIMs utilizing In(OTf)3 in octylmethylimidazolium hexafluorophosphate as ionic liquid.
Scheme 38: FeCl3·6H2O-catalyzed synthesis of BIMs with use of ionic liquid.
Scheme 39: Synthesis of BIMs utilizing the [hmim]HSO4/EtOH catalytic system.
Scheme 40: Synthesis of BIMs utilizing acidic ionic liquid immobilized on silica gel (ILIS-SO2Cl).
Scheme 41: The [bmim][MeSO4]-catalyzed reaction of indole with various aldehydes.
Scheme 42: The role of [bmim][MeSO4] in catalyzing the reaction of indole with aldehydes.
Scheme 43: Synthesis of BIMs utilizing FeCl3-based ionic liquid ([BTBAC]Cl-FeCl3) as catalyst.
Scheme 44: Synthesis of BIMs using [Msim]Cl at room temperature.
Scheme 45: [Et3NH][H2PO4]-catalyzed synthesis of bis(indolyl)methanes.
Scheme 46: PILs-catalyzed synthesis of bis(indolyl)methanes.
Scheme 47: FSILs-mediated synthesis of bis(indolyl)methanes.
Scheme 48: Possible “release and catch” catalytic process.
Scheme 49: Synthesis of bis(indolyl)methanes by [DABCO-H][HSO4].
Scheme 50: Synthesis of bis(indolyl)methanes by [(THA)(SO4)].
Scheme 51: Synthesis of BBSI-Cl and BBSI-HSO4.
Scheme 52: Synthesis of BIMs in the presence of BBSI-Cl and BBSI-HSO4.
Scheme 53: Chemoselectivity of the present method.
Scheme 54: Synthesis of BIMs catalyzed by chitosan-supported ionic liquid.
Scheme 55: Proposed mechanism of action of CSIL.
Scheme 56: Optimization of the reaction in DESs.
Scheme 57: Synthesis of BIMs using ChCl/SnCl2 as DES.
Scheme 58: Synthesis of BIMs derivatives in presence of DES.
Scheme 59: BIMs synthesis in choline chloride/urea (CC/U).
Scheme 60: Flow chemistry-based synthesis of BIMs by Ley.
Scheme 61: Flow chemistry-based synthesis of BIMs proposed by Nam et al.
Scheme 62: Amino-catalyzed reaction of indole with propionaldehyde.
Scheme 63: Aminocatalytic synthesis of BIMs.
Scheme 64: Proposed mechanism for the aminocatalytic synthesis of BIMs.
Scheme 65: Enzymatic reaction of indole with aldehydes.
Scheme 66: Proposed mechanism for the synthesis of BIMs catalyzed by TLIM.
Scheme 67: Proposed reaction mechanism by Badsara.
Scheme 68: Mechanism proposed by D’Auria.
Scheme 69: Photoinduced thiourea catalysis.
Scheme 70: Proposed mechanism of photoacid activation.
Scheme 71: Proposed mechanism of action for CF3SO2Na.
Scheme 72: Proposed mechanism for the synthesis of BIMs by Mandawad.
Scheme 73: Proposed mechanism for the (a) acid generation and (b) synthesis of BIMs.
Scheme 74: a) Reaction conditions employed by Khaksar and b) activation of the carbonyl group by HFIP.
Scheme 75: Activation of the carbonyl group by the PPy@CH2Br through the formation of a halogen bond.
Scheme 76: Reaction conditions utilized by Mhaldar et al.
Scheme 77: a) Reaction conditions employed by López and b) activation of the carbonyl group by thiourea.
Scheme 78: Infrared irradiation approach introduced by Luna-Mora and his research group.
Scheme 79: Synthesis of BIMs with the use of the Fe–Zn BMOF.
Beilstein J. Org. Chem. 2024, 20, 125–154, doi:10.3762/bjoc.20.13
Graphical Abstract
Scheme 1: Pathway of the [2 + 2] CA–RE reaction of an electron-rich alkyne with TCNE or TCNQ. EDG = electron-...
Scheme 2: Reaction pathway for DMA-appended acetylene and TCNEO.
Scheme 3: Pathway of the [2 + 2] CA–RE reaction between 1 and DCFs.
Scheme 4: Sequential double [2 + 2] CA–RE reactions between 1 and TCNE.
Scheme 5: Divergent chemical transformation pathways of TCBD 6.
Scheme 6: Synthesis of 12.
Scheme 7: [2 + 2] CA–RE reaction of 1 with 14. TCE = 1,1,2,2-tetrachloroethane.
Scheme 8: Autocatalytic model proposed by Nielsen et al.
Scheme 9: Synthesis of anthracene-embedded TCBD compound 19.
Scheme 10: Sequence of the [2 + 2] CA–RE reaction between dibenzo-fused cyclooctyne or cyclooctadiyne and TCNE...
Scheme 11: [2 + 2] CA–RE reaction between the CPP derivatives and TCNE. THF = tetrahydrofuran.
Scheme 12: [2 + 2] CA–RE reaction between ethynylfullerenes 31 and TCNE and subsequent thermal rearrangement.
Scheme 13: Pathway of the [2 + 2] CA–RE reaction between TCNE and 34, followed by additional skeletal transfor...
Scheme 14: Synthesis scheme for heterocycle 38 from the reaction between TCNE and 1 in water and a surfactant.
Scheme 15: Synthesis scheme of the CDA product 41.
Scheme 16: Synthesis of rotaxanes 44 and 46 via the [2 + 2] CA–RE reaction.
Scheme 17: Synthesis of a CuI bisphenanthroline-based rotaxane 50.
Figure 1: Structures of the chiral push–pull chromophores 51–56.
Figure 2: Structures of the axially chiral TCBD 57 and DCNQ 58 bearing a C60 core.
Figure 3: Structures of the axially chiral SubPc–TCBD–aniline conjugates 59 and 60 and the subporphyrin–TCBD–...
Figure 4: Structures of 63 and the TCBD 64.
Figure 5: Structures of the fluorophore-containing TCBDs 65–67.
Figure 6: Structures of the fluorophore-containing TCBDs 68–72.
Figure 7: Structures of the urea-containing TCBDs 73–75.
Figure 8: Structures of the fullerene–TCBD and DCNQ conjugates 76–79 and their reference compounds 80–83.
Figure 9: Structures of the ZnPc–TCBD–aniline conjugates 84 and 85.
Figure 10: Structures of the ZnP–PCBD and TCBD conjugates 86–88.
Figure 11: Structures of the porphyrin-based donor–acceptor conjugates (89–104).
Figure 12: Structures of the porphyrin–PTZ or DMA conjugates 105–112.
Figure 13: Structures of the BODIPY–Acceptor–TPA or PTZ conjugates 113–116.
Figure 14: Structures of the corrole–TCBD conjugates 117 and 118.
Figure 15: Structure of the dendritic TCBD 119.
Figure 16: Structures of the TCBDs 120–126.
Figure 17: Structures of the precursor 127 and TCBDs 128–130.
Figure 18: Structures of 131–134 utilized for BHJ OSCs.
Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116
Graphical Abstract
Scheme 1: Oxidation of catechol and subsequent cross-linking. Scheme 1 redrawn from [3].
Scheme 2: (A) Structure of typical urushiol in Chinese lacquer, and (B) schematic process of laccase-catalyze...
Scheme 3: A) Primary amino acid sequence of mfp-1, mfp-3, and mfp-5 (Y: DOPA, K: lysine). B) Scheme showing e...
Scheme 4: Activation–deactivation equilibrium in nitroxide-mediated polymerizations. Bicomponent initiating s...
Scheme 5: Mechanism of a transition metal complex-mediated ATRP. Scheme 5 redrawn from [14].
Scheme 6: Mechanism of RAFT polymerization. Scheme 6 redrawn from [68].
Scheme 7: Degenerative transfer (a) and reversible termination (b) mechanism of OMRP. Scheme 7 redrawn from [70].
Scheme 8: Simplified mechanism of a RITP. Scheme 8 redrawn from [21].
Scheme 9: (A) Structures of π-conjugated conductive polymers. (B) Examples of conductive polymer synthesis vi...
Scheme 10: Possible regiochemical couplings in PATs. Scheme 10 redrawn from [79].
Scheme 11: General thiol-ene photopolymerization process. Scheme 11 redrawn from [81].
Scheme 12: (a) Three generations of Grubbs catalysts. (b) Proposed mechanism for photo-ROMP via a reductive qu...
Scheme 13: Pyrylium and thiopyrylium salts studied by Boydston et al. Scheme 13 redrawn from [91].
Scheme 14: A general illustration of post-polymerization modification by thiol–ene chemistry.
Scheme 15: Introduction of functionalities by nitroxide radical coupling of HO-TEMPO derivatives.
Scheme 16: Chemical reaction process scheme of DCP-induced crosslinking of LDPE. Scheme 16 redrawn from [126].
Scheme 17: A probable mechanism of radical-induced hydrosilylation.
Scheme 18: Polymer surface modification by homolytic dediazonation of diazonium salts.
Scheme 19: Photoinduced polymer surface modification or surface grafting using benzophenone.
Scheme 20: Depolymerization mechanism of common photoresists. (a) A possible mechanism of radiation decomposit...
Scheme 21: Proposed mechanisms of photooxidative depolymerization of polystyrene. (a) Scheme 21a was reprinted with perm...
Beilstein J. Org. Chem. 2023, 19, 1015–1020, doi:10.3762/bjoc.19.77
Graphical Abstract
Figure 1: Schematic representation of the AGA process (A). Variables that can affect the AGA outcome investig...
Figure 2: AGA of model glycan sequences analyzed in this study: α-1,6-linked dimannosides 1, 2 (A), branched ...
Figure 3: Representative HPLC traces for the crude compounds 1 (A), 3 (B), and 5a (C) after cleavage from the...
Beilstein J. Org. Chem. 2023, 19, 956–981, doi:10.3762/bjoc.19.72
Graphical Abstract
Scheme 1: First organocatalyzed asymmetric aza-Friedel–Crafts reaction.
Scheme 2: Aza-Friedel–Crafts reaction between indoles and cyclic ketimines.
Scheme 3: Aza-Friedel–Crafts reaction utilizing trifluoromethyldihydrobenzoazepinoindoles as electrophiles.
Scheme 4: Aza-Friedel–Crafts reaction utilizing cyclic N-sulfimines as electrophiles.
Scheme 5: Aza-Friedel–Crafts reaction involving N-unprotected imino ester as electrophile.
Scheme 6: Aza-Friedel–Crafts and lactonization cascade.
Scheme 7: One-pot oxidation and aza-Friedel–Crafts reaction.
Scheme 8: C1 and C2-symmetric phosphoric acids as catalysts.
Scheme 9: Aza-Friedel–Crafts reaction using Nps-iminophosphonates as electrophiles.
Scheme 10: Aza-Friedel–Crafts reaction between indole and α-iminophosphonate.
Scheme 11: [2.2]-Paracyclophane-derived chiral phosphoric acids as catalyst.
Scheme 12: Aza-Friedel–Crafts reaction through ring opening of sulfamidates.
Scheme 13: Isoquinoline-1,3(2H,4H)-dione scaffolds as electrophiles.
Scheme 14: Functionalization of the carbocyclic ring of substituted indoles.
Scheme 15: Aza-Friedel–Crafts reaction between unprotected imines and aza-heterocycles.
Scheme 16: Anilines and α-naphthols as potential nucleophiles.
Scheme 17: Solvent-controlled regioselective aza-Friedel–Crafts reaction.
Scheme 18: Generating central and axial chirality via aza-Friedel–Crafts reaction.
Scheme 19: Reaction between indoles and racemic 2,3-dihydroisoxazol-3-ol derivatives.
Scheme 20: Exploiting 5-aminoisoxazoles as nucleophiles.
Scheme 21: Reaction between unsubstituted indoles and 3-alkynylated 3-hydroxy-1-oxoisoindolines.
Scheme 22: Synthesis of unnatural amino acids bearing an aza-quaternary stereocenter.
Scheme 23: Atroposelective aza-Friedel–Crafts reaction.
Scheme 24: Coupling of 5-aminopyrazole and 3H-indol-3-ones.
Scheme 25: Pyrophosphoric acid-catalyzed aza-Friedel–Crafts reaction on phenols.
Scheme 26: Squaramide-assisted aza-Friedel–Crafts reaction.
Scheme 27: Thiourea-catalyzed aza-Friedel–Crafts reaction.
Scheme 28: Squaramide-catalyzed reaction between β-naphthols and benzothiazolimines.
Scheme 29: Thiourea-catalyzed reaction between β-naphthol and isatin-derived ketamine.
Scheme 30: Quinine-derived molecule as catalyst.
Scheme 31: Cinchona alkaloid as catalyst.
Scheme 32: aza-Friedel–Crafts reaction by phase transfer catalyst.
Scheme 33: Disulfonamide-catalyzed reaction.
Scheme 34: Heterogenous thiourea-catalyzed aza-Friedel–Crafts reaction.
Scheme 35: Total synthesis of (+)-gracilamine.
Scheme 36: Total synthesis of (−)-fumimycin.
Beilstein J. Org. Chem. 2022, 18, 1720–1740, doi:10.3762/bjoc.18.182
Graphical Abstract
Scheme 1: Automated in-line chromatography with the Advion puriFlash® system. The rightmost part of the schem...
Scheme 2: Purification via pH tuning and several Zaiput membranes. Redrawn from [51].
Scheme 3: Two-phase recirculating system for purifications of an immobilized enzyme-based reaction. Redrawn f...
Scheme 4: Countercurrent L–L purification using large Zaiput membranes in the presence of a phase transfer ca...
Scheme 5: General scheme of a telescoped flow process using L–L separators.
Scheme 6: Example of phase separation using a computer-vision approach. Redrawn from [68].
Scheme 7: Example of an inline purification using heterogeneous scavenging. Redrawn from [76].
Scheme 8: General scheme of a telescoped process using heterogenous cartridges.
Scheme 9: Comparison of two strategies for flow-based imatinib syntheses. Redrawn from [91] and [92].
Scheme 10: General purification scheme using the catch and release strategy.
Scheme 11: Exemplar catch and release purification of a stereoselective oxidation. Redrawn from [105].
Scheme 12: Catch and release-type purification using conventional SiO2. Redrawn from [107].
Scheme 13: Schematic representation of an industrial continuous crystallization. Redrawn from [109].
Scheme 14: General scheme of an academic inline crystallization approach.
Scheme 15: Simplified overview of purification options and selected criteria.
Beilstein J. Org. Chem. 2022, 18, 1471–1478, doi:10.3762/bjoc.18.154
Graphical Abstract
Figure 1: Chiral phosphorus acids (CPAs) derived from BINOL, VAPOL, and SPINOL. R = H, Ph, 4-PhC6H4-, 4-β-nap...
Scheme 1: The thiolic/thionic tautomeric equilibrium in thiophosphorus acids.
Figure 2: Project strategy and requirements for C1-symmetrical CPAs.
Figure 3: BINOL CPA and C1-symmetrical CPA targets 1–4.
Scheme 2: Synthesis of tryptophol-derived thiophosphorus acid 1.
Scheme 3: Synthesis of indole-derived thiophosphorus acid 2.
Scheme 4: Synthesis of N-biphenyl-DOPO CPA 4.
Scheme 5: Transfer hydrogenation of 2-phenylquinoline and transition-state proposed by Guinchard and coworker...
Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43
Graphical Abstract
Figure 1: Natural bioactive naphthoquinones.
Figure 2: Chemical structures of vitamins K.
Figure 3: Redox cycle of menadione.
Scheme 1: Selected approaches for menadione synthesis using silver(I) as a catalyst.
Scheme 2: Methylation approaches for the preparation of menadione from 1,4-naphthoquinone using tert-butyl hy...
Scheme 3: Methylation approach of 1,4-naphthoquinone using i) rhodium complexes/methylboronic acid and ii) bi...
Scheme 4: Synthesis of menadione (10) from itaconic acid.
Scheme 5: Menadione synthesis via Diels–Alder reaction.
Scheme 6: Synthesis of menadione (10) using p-cresol as a synthetic precursor.
Scheme 7: Synthesis of menadione (10) via demethoxycarbonylating annulation of methyl methacrylate.
Scheme 8: Furan 34 used as a diene in a Diels–Alder reaction for the synthesis of menadione (10).
Scheme 9: o-Toluidine as a dienophile in a Diels–Alder reaction for the synthesis of menadione (10).
Scheme 10: Representation of electrochemical synthesis of menadione.
Figure 4: Reaction sites and reaction types of menadione as substrate.
Scheme 11: DBU-catalyzed epoxidation of menadione (10).
Scheme 12: Phase-transfer catalysis for the epoxidation of menadione.
Scheme 13: Menadione epoxidation using a hydroperoxide derived from (+)-norcamphor.
Scheme 14: Enantioselective Diels–Alder reaction for the synthesis of asymmetric quinone 50 catalyzed by a chi...
Scheme 15: Optimized reaction conditions for the synthesis of anthra[9,1-bc]pyranone.
Scheme 16: Synthesis of anthra[9,1-bc]furanone, anthra[9,1-bc]pyridine, and anthra[9,1-bc]pyrrole derivatives.
Scheme 17: Synthesis of derivatives employing protected trienes.
Scheme 18: Synthesis of cyclobutene derivatives of menadione.
Scheme 19: Menadione reduction reactions using sodium hydrosulfite.
Scheme 20: Green methodology for menadiol synthesis and pegylation.
Scheme 21: Menadione reduction by 5,6-O-isopropylidene-ʟ-ascorbic acid under UV light irradiation.
Scheme 22: Selected approaches of menadione hydroacetylation to diacetylated menadiol.
Scheme 23: Thiele–Winter reaction catalyzed by Bi(OTf)3.
Scheme 24: Carbonyl condensation of menadione using resorcinol and a hydrazone derivative.
Scheme 25: Condensation reaction of menadione with thiosemicarbazide.
Scheme 26: Condensation reaction of menadione with acylhydrazides.
Scheme 27: Menadione derivatives functionalized with organochalcogens.
Scheme 28: Synthesis of selenium-menadione conjugates derived from chloromethylated menadione 84.
Scheme 29: Menadione alkylation by the Kochi–Anderson method.
Scheme 30: Menadione alkylation by diacids.
Scheme 31: Menadione alkylation by heterocycles-substituted carboxylic acids.
Scheme 32: Menadione alkylation by bromoalkyl-substituted carboxylic acids.
Scheme 33: Menadione alkylation by complex carboxylic acids.
Scheme 34: Kochi–Anderson method variations for the menadione alkylation via oxidative decarboxylation of carb...
Scheme 35: Copper-catalyzed menadione alkylation via free radicals.
Scheme 36: Nickel-catalyzed menadione cyanoalkylation.
Scheme 37: Iron-catalyzed alkylation of menadione.
Scheme 38: Selected approaches to menadione alkylation.
Scheme 39: Menadione acylation by photo-Friedel–Crafts acylation reported by Waske and co-workers.
Scheme 40: Menadione acylation by Westwood procedure.
Scheme 41: Synthesis of 3-benzoylmenadione via metal-free TBAI/TBHP system.
Scheme 42: Michael-type addition of amines to menadione reported by Kallmayer.
Scheme 43: Synthesis of amino-menadione derivatives using polyalkylamines.
Scheme 44: Selected examples for the synthesis of different amino-substituted menadione derivatives.
Scheme 45: Selected examples of Michael-type addition of complex amines to menadione (10).
Scheme 46: Addition of different natural α-amino acids to menadione.
Scheme 47: Michael-type addition of amines to menadione using silica-supported perchloric acid.
Scheme 48: Indolylnaphthoquinone or indolylnaphthalene-1,4-diol synthesis reported by Yadav et al.
Scheme 49: Indolylnaphthoquinone synthesis reported by Tanoue and co-workers.
Scheme 50: Indolylnaphthoquinone synthesis from menadione by Escobeto-González and co-workers.
Scheme 51: Synthesis of menadione analogues functionalized with thiols.
Scheme 52: Synthesis of menadione-derived symmetrical derivatives through reaction with dithiols.
Scheme 53: Mercaptoalkyl acids as nucleophiles in Michael-type addition reaction to menadione.
Scheme 54: Reactions of menadione (10) with cysteine derivatives for the synthesis of quinoproteins.
Scheme 55: Synthesis of menadione-glutathione conjugate 152 by Michael-type addition.
Beilstein J. Org. Chem. 2021, 17, 2894–2905, doi:10.3762/bjoc.17.197
Graphical Abstract
Figure 1: Molecular structures of emitters.
Figure 2: a) Molecular structure and b) optimized DFT-calculated geometry of DICzTRZ. Hydrogen atoms are omit...
Figure 3: HOMO, HOMO–1 (H–1), LUMO, and LUMO+1 (L+1) electron density distributions (isovalue: 0.02) and ener...
Figure 4: a) Cyclic voltammetry (CV) and differential pulse voltammetry (DPV) of DICzTRZ in DCM (scan rate = ...
Figure 5: a) Prompt and b) delayed time-resolved decay in spin-coated 20 wt % CzSi film of DICzTRZ (λexc = 37...
Figure 6: Angle-resolved photoluminescence measurement of a solution-processed film of 20 wt % DICzTRZ in CzS...
Figure 7: Device characteristics of 20 and 30 wt % DICzTRZ-based OLEDs, which are represented by red and blue...
Figure 8: Device efficiency simulation of the fabricated OLEDs depicting the variation in EQE with varied PL ...
Beilstein J. Org. Chem. 2021, 17, 2553–2569, doi:10.3762/bjoc.17.171
Graphical Abstract
Figure 1: Schematic representation of the process of aqueous cryogel formation, using (a) monomers/small mole...
Figure 2: Microarchitecture of gelatin cryogels. (A) Surface and cross-sectional SEM micrographs of highly po...
Figure 3: Principle of 3D-cryogel printing. A) Illustration of 3D-printing of cryogels. B) Illustration of th...
Figure 4: Illustration of the production of the injectable multifunctional composite, comprised of alginate c...
Figure 5: Digital and SEM photographs of PETEGA cryogel at 20 °C (top) and 50 °C (bottom), synthesised via UV...
Figure 6: Cell morphology of T47D breast cancer cells cultured in HA cryogels. (A) Schematic representation o...
Figure 7: Preparation of PDMA/β-CD cryogel via cryogenic treatment and photochemical crosslinking in frozen s...
Figure 8: (A) Healing rate of wounds treated with autoclaved CG11 cryogels and those treated with 70% ethanol...
Figure 9: In vivo haemostatic capacity evaluation of the cryogels. Blood loss (a) and haemostatic time (b) in...
Beilstein J. Org. Chem. 2021, 17, 2477–2487, doi:10.3762/bjoc.17.164
Graphical Abstract
Figure 1: Structures of azide and alkyne functional molecules and polymers used in the photoinduced CuAAC rea...
Figure 2: UV–vis spectra of CuICl, CuIICl2 and BPNs.
Figure 3: a) 1H NMR spectra of the model reaction between benzyl azide (Az-1) and phenylacetylene (Alk-3) bef...
Scheme 1: Proposed mechanism for photoinduced CuAAC reaction using exfoliated BPNs.
Figure 4: a) 1H NMR spectrum of chain end modified PCL-Anth; b) UV–vis spectra of (azidomethyl)anthracene (bl...
Scheme 2: Synthesis of PS-b-PCL block copolymer via exfoliated BPNs-mediated photoinduced CuAAC reaction.
Figure 5: a) GPC traces of PS-Az, PCL-Alk and block copolymer (Ps-b-PCL) b) 1H NMR spectrum of the block copo...
Scheme 3: Preparation of the cross-linked polymer by CuAAC reaction using multifunctional monomers, Az-3 and ...
Figure 6: a) DSC thermogram of photoinduced synthesis of nanocomposite networks (heating rate: 10 °C/min). b)...
Figure 7: (a, b) TEM images of cross-linked polymer at two different magnifications, c) HAADF-STEM image and ...
Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138
Graphical Abstract
Figure 1: (a) Schematic representation of the phase stability of a binary mixture based on the free enthalpy ...
Figure 2: Illustration of the relationship between the type of miscibility gap and the temperature dependence...
Figure 3: Schematically pictured phase diagram of a binary mixture composed of a dissolved polymer with a LCS...
Figure 4: Schematic illustration of a thermo-induced swelling behavior of a star polymer composed of responsi...
Figure 5: Schematic illustration of self-assembly of block copolymer amphiphiles in a polar medium.
Figure 6: Schematic comparison of the size and conformation between free polymer chains (a), grafted polymer ...
Figure 7: Comparison of the possible phase diagrams of a polymer in solution with partially miscibility and t...
Figure 8: Selection of polymers exhibiting UCST behavior due to hydrogen bonding (blue) divided into homo- (a...
Figure 9: Part A shows the molecular structure of PDMAPS stars synthesized by Li et al. (left) demonstrating ...
Figure 10: Part A contains a schematic demonstration of conformational transitions of dual-thermoresponsive bl...
Figure 11: Part A pictures zwitterionic brushes grafted from silicon substrates obtaining a nonassociated, hyd...
Figure 12: Part A pictures the UCST phase transition of zwitterionic polymers grafted on the surface of mesopo...