Search for "electron donor" in Full Text gives 172 result(s) in Beilstein Journal of Organic Chemistry.
Beilstein J. Org. Chem. 2025, 21, 515–525, doi:10.3762/bjoc.21.39
Graphical Abstract
Scheme 1: List of reactions, experimental conditions and yields studied in this work.
Figure 1: Top: 379 MHz 19F NMR spectrum of 9,10-ANTH(BnF)2 in CDCl3. Bottom: absorption (aerobic, solid line)...
Figure 2: Top: X-ray structure of 9,10-ANTH(BnF)2, thermal ellipsoids 50% probability. Bottom: a view down th...
Figure 3: Absorption spectra of ANTH and 9,10-ANTH(BnF)2 in CH2Cl2 recorded over the period of 53 days in air...
Figure 4: Direct analysis in real time (DART) positive ion mass spectrum of the photoirradiated 9,10-ANTH(BnF)...
Figure 5: The % remaining of ANTH and 9,10-ANTH(BnF)2 dissolved in CDCl3 upon irradiation. Resonances δ = 7.4...
Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33
Graphical Abstract
Figure 1: The Grotthuss–Draper, Einstein–Stark, and Beer–Lambert laws. T: transmittance; ε: molar attenuation...
Figure 2: The benefits of merging photochemistry with mechanochemical setups (top). Most common setups for ph...
Scheme 1: Mechanochemically triggered pedal-like motion in solid-state [2 + 2] photochemical cycloaddition fo...
Scheme 2: Mechanically promoted [2 + 2] photodimerization of trans-1,2-bis(4-pyridyl)ethylene (2.1) via supra...
Scheme 3: Photo-thermo-mechanosynthesis of quinolines [65].
Scheme 4: Study of the mechanically assisted [2 + 2] photodimerization of chalcone [66].
Scheme 5: Liquid-assisted vortex grinding (LAVG) for the synthesis of [2.2]paracyclophane [68].
Scheme 6: Photomechanochemical approach for the riboflavin tetraacetate-catalyzed photocatalytic oxidation of...
Scheme 7: Photomechanochemical oxidation of 1,2-diphenylethyne to benzil. The photo in Scheme 7 was republished with ...
Scheme 8: Photomechanochemical borylation of aryldiazonium salts. The photo in Scheme 8 was reproduced from [72] (© 2017 ...
Scheme 9: Photomechanochemical control over stereoselectivity in the [2 + 2] dimerization of acenaphthylene. ...
Scheme 10: Photomechanochemical synthesis of polyaromatic compounds using UV light. The photo in Scheme 10 was reproduc...
Scheme 11: Mechanically assisted photocatalytic reactions: A) atom-transfer-radical addition, B) pinacol coupl...
Scheme 12: Use of mechanoluminescent materials as photon sources for photomechanochemistry. SAOED: SrAl2O4:Eu2+...
Figure 3: SWOT (strengths, weaknesses, opportunities, threats) analysis of photomechanochemistry.
Beilstein J. Org. Chem. 2025, 21, 55–121, doi:10.3762/bjoc.21.6
Graphical Abstract
Scheme 1: Formation of axially chiral styrenes 3 via iminium activation.
Scheme 2: Synthesis of axially chiral 2-arylquinolines 6.
Scheme 3: Atroposelective intramolecular (4 + 2) annulation leading to aryl-substituted indolines.
Scheme 4: Atroposelective formation of biaryl via twofold aldol condensation.
Scheme 5: Strategy towards diastereodivergent formation of axially chiral oligonaphthylenes.
Scheme 6: Atroposelective formation of chiral biaryls based on a Michael/Henry domino reaction.
Scheme 7: Organocatalytic Michael/aldol cascade followed by oxidative aromatization.
Scheme 8: Atroposelective formation of C(sp2)–C(sp3) axially chiral compounds.
Scheme 9: NHC-catalyzed synthesis of axially chiral styrenes 26.
Scheme 10: NHC-catalyzed synthesis of biaxial chiral pyranones.
Scheme 11: Formation of bridged biaryls with eight-membered lactones.
Scheme 12: The NHC-catalyzed (3 + 2) annulation of urazoles 37 and ynals 36.
Scheme 13: NHC-catalyzed synthesis of axially chiral 4‑aryl α‑carbolines 41.
Scheme 14: NHC-catalyzed construction of N–N-axially chiral pyrroles and indoles.
Scheme 15: NHC-catalyzed oxidative Michael–aldol cascade.
Scheme 16: NHC-catalyzed (4 + 2) annulation for the synthesis of benzothiophene-fused biaryls.
Scheme 17: NHC-catalyzed desymmetrization of N-aryl maleimides.
Scheme 18: NHC-catalyzed deracemization of biaryl hydroxy aldehydes 55a–k into axially chiral benzonitriles 56a...
Scheme 19: NHC-catalyzed desymmetrization of 2-aryloxyisophthalaldehydes.
Scheme 20: NHC-catalyzed DKR of 2-arylbenzaldehydes 62.
Scheme 21: Atroposelective biaryl amination.
Scheme 22: CPA-catalyzed atroposelective amination of 2-anilinonaphthalenes.
Scheme 23: Atroposelective DKR of naphthylindoles.
Scheme 24: CPA-catalyzed kinetic resolution of binaphthylamines.
Scheme 25: Atroposelective amination of aromatic amines with diazodicarboxylates.
Scheme 26: Atroposelective Friedländer heteroannulation.
Scheme 27: CPA-catalyzed formation of axially chiral 4-arylquinolines.
Scheme 28: CPA-catalyzed Friedländer reaction of arylketones with cyclohexanones.
Scheme 29: CPA-catalyzed atroposelective Povarov reaction.
Scheme 30: Atroposelective CPA-catalyzed Povarov reaction.
Scheme 31: Paal–Knorr formation of axially chiral N-pyrrolylindoles and N-pyrrolylpyrroles.
Scheme 32: Atroposelective Paal–Knorr reaction leading to N-pyrrolylpyrroles.
Scheme 33: Atroposelective Pictet–Spengler reaction of N-arylindoles with aldehydes.
Scheme 34: Atroposelective Pictet–Spengler reaction leading to tetrahydroisoquinolin-8-ylanilines.
Scheme 35: Atroposelective formation of arylindoles.
Scheme 36: CPA-catalyzed arylation of naphthoquinones with indolizines.
Scheme 37: Atroposelective reaction of o-naphthoquinones.
Scheme 38: CPA-catalyzed formation of axially chiral arylquinones.
Scheme 39: CPA-catalyzed axially chiral N-arylquinones.
Scheme 40: Atroposelective additions of bisindoles to isatin-based 3-indolylmethanols.
Scheme 41: CPA-catalyzed synthesis of axially chiral arylindolylindolinones.
Scheme 42: CPA-catalyzed reaction between bisindoles and ninhydrin-derived 3-indoylmethanols.
Scheme 43: Atroposelective reaction of bisindoles and isatin-derived imines.
Scheme 44: CPA-catalyzed formation of axially chiral bisindoles.
Scheme 45: Atroposelective reaction of 2-naphthols with alkynylhydroxyisoindolinones.
Scheme 46: CPA-catalyzed reaction of indolylnaphthols with propargylic alcohols.
Scheme 47: Atroposelective formation of indolylpyrroloindoles.
Scheme 48: Atroposelective reaction of indolylnaphthalenes with alkynylnaphthols.
Scheme 49: CPA-catalyzed addition of naphthols to alkynyl-2-naphthols and 2-naphthylamines.
Scheme 50: CPA-catalyzed formation of axially chiral aryl-alkene-indoles.
Scheme 51: CPA-catalyzed formation of axially chiral styrenes.
Scheme 52: Atroposelective formation of alkenylindoles.
Scheme 53: Atroposelective formation of axially chiral arylquinolines.
Scheme 54: Atroposelective (3 + 2) cycloaddition of alkynylindoles with azonaphthalenes.
Scheme 55: CPA-catalyzed formation of axially chiral 3-(1H-benzo[d]imidazol-2-yl)quinolines.
Scheme 56: Atroposelective cyclization of 3-(arylethynyl)-1H-indoles.
Scheme 57: Atroposelective three-component heteroannulation.
Scheme 58: CPA-catalyzed formation of arylbenzimidazols.
Scheme 59: CPA-catalyzed reaction of N-naphthylglycine esters with nitrosobenzenes.
Scheme 60: CPA-catalyzed formation of axially chiral N-arylbenzimidazoles.
Scheme 61: CPA-catalyzed formation of axially chiral arylbenzoindoles.
Scheme 62: CPA-catalyzed formation of pyrrolylnaphthalenes.
Scheme 63: CPA-catalyzed addition of naphthols and indoles to nitronaphthalenes.
Scheme 64: Atroposelective reaction of heterobiaryl aldehydes and aminobenzamides.
Scheme 65: Atroposelective cyclization forming N-arylquinolones.
Scheme 66: Atroposelective formation of 9H-carbazol-9-ylnaphthalenes and 1H-indol-1-ylnaphthalene.
Scheme 67: CPA-catalyzed formation of pyrazolylnaphthalenes.
Scheme 68: Atroposelective addition of diazodicarboxamides to azaborinephenols.
Scheme 69: Catalytic formation of axially chiral arylpyrroles.
Scheme 70: Atroposelective coupling of 1-azonaphthalenes with 2-naphthols.
Scheme 71: CPA-catalyzed formation of axially chiral oxindole-based styrenes.
Scheme 72: Atroposelective electrophilic bromination of aminonaphthoquinones.
Scheme 73: Atroposelective bromination of dienes.
Scheme 74: CPA-catalyzed formation of axially chiral 5-arylpyrimidines.
Scheme 75: Atroposelective hydrolysis of biaryloxazepines.
Scheme 76: Atroposelective opening of dinaphthosiloles.
Scheme 77: Atroposelective reduction of naphthylenals.
Scheme 78: Atroposelective allylic substitution with 2-naphthols.
Scheme 79: Atroposelective allylic alkylation with phosphinamides.
Scheme 80: Atroposelective allylic substitution with aminopyrroles.
Scheme 81: Atroposelective allylic substitution with aromatic sulfinamides.
Scheme 82: Atroposelective sulfonylation of naphthylynones.
Scheme 83: Squaramide-catalyzed reaction of alkynyl-2-naphthols with 5H-oxazolones.
Scheme 84: Formation of axially chiral styrenes via sulfonylative opening of cyclopropanols.
Scheme 85: Atroposelective organo-photocatalyzed sulfonylation of alkynyl-2-naphthols.
Scheme 86: Thiourea-catalyzed atroposelective cyclization of alkynylnaphthols.
Scheme 87: Squaramide-catalyzed formation of axially chiral naphthylisothiazoles.
Scheme 88: Atroposelective iodo-cyclization catalyzed by squaramide C69.
Scheme 89: Squaramide-catalyzed formation of axially chiral oligoarenes.
Scheme 90: Atroposelective ring-opening of cyclic N-sulfonylamides.
Scheme 91: Thiourea-catalyzed kinetic resolution of naphthylpyrroles.
Scheme 92: Atroposelective ring-opening of arylindole lactams.
Scheme 93: Atroposelective reaction of 1-naphthyl-2-tetralones and diarylphosphine oxides.
Scheme 94: Atroposelective reaction of iminoquinones with indoles.
Scheme 95: Kinetic resolution of binaphthylalcohols.
Scheme 96: DKR of hydroxynaphthylamides.
Scheme 97: Atroposelective N-alkylation with phase-transfer catalyst C75.
Scheme 98: Atroposelective allylic substitution via kinetic resolution of biarylsulfonamides.
Scheme 99: Atroposelective bromo-functionalization of alkynylarenes.
Scheme 100: Sulfenylation-induced atroposelective cyclization.
Scheme 101: Atroposelective O-sulfonylation of isochromenone-indoles.
Scheme 102: NHC-catalyzed atroposelective N-acylation of anilines.
Scheme 103: Peptide-catalyzed atroposelective ring-opening of lactones.
Scheme 104: Peptide-catalyzed coupling of 2-naphthols with quinones.
Scheme 105: Atroposelective nucleophilic aromatic substitution of fluoroarenes.
Beilstein J. Org. Chem. 2024, 20, 3299–3305, doi:10.3762/bjoc.20.274
Graphical Abstract
Scheme 1: Preparation of key intermediate 5.
Scheme 2: Synthesis of PhFlOP-based molecules 7.
Figure 1: An ORTEP drawing obtained using the X-ray crystallographic data of 7-H.
Figure 2: (a) UV–vis absorption spectra of the PhFlOP-based emitters 7 measured at a concentration of ≈10−5 M...
Figure 3: (a) PL spectra of the PhFlOP-based emitters 7 measured in toluene at room temperature. (b) PL spect...
Beilstein J. Org. Chem. 2024, 20, 3274–3280, doi:10.3762/bjoc.20.271
Graphical Abstract
Figure 1: Giese reaction: Radical addition on olefins with an electron-withdrawing group (EWG) followed by a ...
Figure 2: Alkyl bromide and Dha derivative scope. Reaction conditions: Dha derivative (0.5 mmol), alkyl bromi...
Figure 3: Scaled-up reaction. Reaction conditions: Dha derivative (2.2 mmol), alkyl bromide (5.4 mmol), tris(...
Beilstein J. Org. Chem. 2024, 20, 3085–3112, doi:10.3762/bjoc.20.257
Graphical Abstract
Figure 1: Chemical structures of the main tetrapyrrolic macrocycles studied in this review for their role as ...
Figure 2: Calix[4]pyrroles 3 and 4 and an their acyclic analogue 5 used for the transformation of Danishefsky...
Figure 3: Calixpyrrole-based organocatalysts 11 and 12 for the diastereoselective addition reaction of TMSOF ...
Figure 4: (a) Chemical structures of macrocyclic organocatalysts used for the synthesis of cyclic carbonates ...
Figure 5: Cuprous chloride-catalyzed aziridination of styrene (22) by chloramine-T (23) providing 1-tosyl-2-p...
Figure 6: Chemical structures of the various porphyrin macrocycles (18, 25–41) screened as potential catalyst...
Figure 7: Organocatalytic activity of distorted porphyrins explored by Senge and co-workers. Planar macrocycl...
Figure 8: Chemical structures of H2EtxTPP (x = 0, 2, 4, 6, 8) compounds with incrementally increasing nonplan...
Figure 9: Chemical structures of OxP macrocycles tested as potential organocatalysts for the conjugate additi...
Figure 10: a) Fundamental structure of the J-aggregates of diprotonated TPPS3 53 and b) its use as a catalyst ...
Figure 11: Chemical structures of amphiphilic porphyrin macrocycles used as pH-switchable catalysts based on i...
Figure 12: a) Chemical structures of porphyrin macrocycles for the cycloaddition of CO2 to N-alkyl/arylaziridi...
Figure 13: Electron and energy-transfer processes typical for excited porphyrin molecules (Por = porphyrin mac...
Figure 14: Proposed mechanism for the light-induced α-alkylation of aldehydes with EDA in the presence of H2TP...
Figure 15: a) Chemical structures of porphyrins screened as photoredox catalysts, b) model reaction of furan (...
Figure 16: Porphyrin macrocycles H2TPP (18) and PPIX 78 as photoreductants for the red light-induced C–H aryla...
Figure 17: Porphyrin macrocycles H2TPP (18) and PPIX 78 as photoredox catalyst for (a) α-alkylation of an alde...
Figure 18: Corrole macrocycles 98–100 as photoredox catalysts for C–H arylation and borylation reactions. Adap...
Figure 19: Proposed catalytic cycle of electrocatalytic generation of H2 evolution using tetrapyrrolic macrocy...
Figure 20: a) Chemical structures of tetrapyrrolic macrocycles 109, 73, and 110 used for oxygen reductions in ...
Figure 21: a) Absorption spectra (left) of the air-saturated DCE solutions containing: 5 × 10−5 M H2TPP (black...
Figure 22: Chemical structures of N,N’-dimethylated saddle-distorted porphyrin isomers, syn-Me2P 111 and anti-...
Figure 23: Reaction mechanisms for the two-electron reduction of O2 by a) syn-Me2Iph 113 and b) anti-Me2Iph 114...
Figure 24: O2/H2O2 interconversion using methylated saddle-distorted porphyrin and isophlorin (reduced porphyr...
Figure 25: Chemical structures of distorted dodecaphenylporphyrin macrocycle 117 and its diprotonated form 118...
Beilstein J. Org. Chem. 2024, 20, 3016–3025, doi:10.3762/bjoc.20.251
Graphical Abstract
Figure 1: Structure of previously synthesized stilbazoles А and arylidene derivatives of pyrindane 1 reported...
Scheme 1: Synthesis of donor–acceptor 1-pyrindane derivatives 1.
Figure 2: 1H,1H-NOESY spectrum of compound 1c in DMSO-d6.
Figure 3: Absorption (left) and normalized emission spectra (right) of compound 1i in various solvents (c = 10...
Scheme 2: Plausible equilibrium of compounds 1i and 1iH+ in acidic solution.
Figure 4: Solvatochromic behavior of compounds 1c and 1i: plots of arithmetic mean of emission/absorption wav...
Figure 5: Absorption spectra of compounds 1a–i in toluene (left) and DMSO (right, c = 10−5 M).
Figure 6: Normalized emission spectra of compounds 1a–i in toluene (left) and DMSO (right, c = 10−5 M).
Figure 7: Photos of fluorescent solutions of compounds 1a–i in toluene (top) and DMSO (bottom) taken under a ...
Figure 8: Normalized solid-state emission spectra of compounds 1a–i (bottom) and photos of powders taken unde...
Beilstein J. Org. Chem. 2024, 20, 2891–2920, doi:10.3762/bjoc.20.243
Graphical Abstract
Figure 1: Various structures of iodonium salts.
Scheme 1: Αrylation of α-fluoroacetoacetamides 5 to α-aryl-α-fluoroacetoacetamides 7 and α-fluoroacetamides 8...
Scheme 2: Proposed mechanism for the arylation of α-fluoroacetoacetamides 5 to α-aryl-α-fluoroacetoacetamides ...
Scheme 3: α-Arylation of α-nitro- and α-cyano derivatives of α-fluoroacetamides 9 employing unsymmetrical DAI...
Scheme 4: Synthesis of α,α-difluoroketones 13 by reacting α,α-difluoro-β-keto acid esters 11 with aryl(TMP)io...
Scheme 5: Coupling reaction of arynes generated by iodonium salts 6 and arynophiles 14 for the synthesis of t...
Scheme 6: Metal-free arylation of quinoxalines 17 and quinoxalinones 19 with DAISs 16.
Scheme 7: Transition-metal-free, C–C cross-coupling of 2-naphthols 21 to 1-arylnapthalen-2-ols 22 employing d...
Scheme 8: Arylation of vinyl pinacol boronates 23 to trans-arylvinylboronates 24 in presence of hypervalent i...
Scheme 9: Light-induced selective arylation at C2 of quinoline N-oxides 25 and pyridine N-oxides 28 in the pr...
Scheme 10: Plaussible mechanism for the light-induced selective arylation of N-heterobiaryls.
Scheme 11: Photoinduced arylation of heterocycles 31 with the help of diaryliodonium salts 16 activated throug...
Scheme 12: Arylation of MBH acetates 33 with DIPEA and DAIRs 16.
Scheme 13: Aryl sulfonylation of MBH acetates 33 with DABSO and diphenyliodonium triflates 16.
Scheme 14: Synthesis of oxindoles 37 from N-arylacrylamides 36 and diaryliodonium salts 26.
Scheme 15: Mechanically induced N-arylation of amines 38 using diaryliodonium salts 16.
Scheme 16: o-Fluorinated diaryliodonium salts 40-mediated diarylation of amines 38.
Scheme 17: Proposed mechanism for the diarylation of amines 38 using o-fluorinated diaryliodonium salts 40.
Scheme 18: Ring-opening difunctionalization of aliphatic cyclic amines 41.
Scheme 19: N-Arylation of amino acid esters 44 using hypervalent iodonium salts 45.
Scheme 20: Regioselective N-arylation of triazole derivatives 47 by hypervalent iodonium salts 48.
Scheme 21: Regioselective N-arylation of tetrazole derivatives 50 by hypervalent iodonium salt 51.
Scheme 22: Selective arylation at nitrogen and oxygen of pyridin-2-ones 53 by iodonium salts 16 depending on t...
Scheme 23: N-Arylation using oxygen-bridged acyclic diaryliodonium salt 56.
Scheme 24: The successive C(sp2)–C(sp2)/O–C(sp2) bond formation of naphthols 58.
Scheme 25: Synthesis of diarylethers 62 via in situ generation of hypervalent iodine salts.
Scheme 26: O-Arylated galactosides 64 by reacting protected galactosides 63 with hypervalent iodine salts 16 i...
Scheme 27: Esterification of naproxen methyl ester 65 via formation and reaction of naproxen-containing diaryl...
Scheme 28: Etherification and esterification products 72 through gemfibrozil methyl ester-derived diaryliodoni...
Scheme 29: Synthesis of iodine containing meta-substituted biaryl ethers 74 by reacting phenols 61 and cyclic ...
Scheme 30: Plausible mechanism for the synthesis of meta-functionalized biaryl ethers 74.
Scheme 31: Intramolecular aryl migration of trifluoromethane sulfonate-substituted diaryliodonium salts 75.
Scheme 32: Synthesis of diaryl ethers 80 via site-selective aryl migration.
Scheme 33: Synthesis of O-arylated N-alkoxybenzamides 83 using aryl(trimethoxyphenyl)iodonium salts 82.
Scheme 34: Synthesis of aryl sulfides 85 from thiols 84 using diaryliodonium salts 16 in basic conditions.
Scheme 35: Base-promoted synthesis of diarylsulfoxides 87 via arylation of general sulfinates 86.
Scheme 36: Plausible mechanism for the arylation of sulfinates 86 via sulfenates A to give diaryl sulfoxides 87...
Scheme 37: S-Arylation reactions of aryl or heterocyclic thiols 88.
Scheme 38: Site-selective S-arylation reactions of cysteine thiol groups in 91 and 94 in the presence of diary...
Scheme 39: The selective S-arylation of sulfenamides 97 using diphenyliodonium salts 98.
Scheme 40: Plausible mechanism for the synthesis of sulfilimines 99.
Scheme 41: Synthesis of S-arylxanthates 102 by reacting DAIS 101 with potassium alkyl xanthates 100.
Figure 2: Structured of the 8-membered and 4-membered heterotetramer I and II.
Scheme 42: S-Arylation by diaryliodonium cations 103 using KSCN (104) as a sulfur source.
Scheme 43: S-Arylation of phosphorothioate diesters 107 through the utilization of diaryliodonium salts 108.
Scheme 44: Transfer of the aryl group from the hypervalent iodonium salt 108 to phosphorothioate diester 107.
Scheme 45: Synthesis of diarylselenides 118 via diarylation of selenocyanate 115.
Scheme 46: Light-promoted arylation of tertiary phosphines 119 to quaternary phosphonium salts 121 using diary...
Scheme 47: Arylation of aminophosphorus substrate 122 to synthesize phosphine oxides 123 using aryl(mesityl)io...
Scheme 48: Reaction of diphenyliodonium triflate (16) with DMSO (124) via thia-Sommelet–Hauser rearrangement.
Scheme 49: Synthesis of biaryl compounds 132 by reacting diaryliodonium salts 131 with arylhydroxylamines 130 ...
Scheme 50: Synthesis of substituted indazoles 134 and 135 from N-hydroxyindazoles 133.
Beilstein J. Org. Chem. 2024, 20, 2732–2738, doi:10.3762/bjoc.20.231
Graphical Abstract
Figure 1: (a) Chemical structure and schematic illustration of the charge-separated state of a triad molecule...
Figure 2: Differential scanning calorimetry analysis for the phase transition of liposomes (1 mM phospholipid...
Figure 3: UV–vis absorption spectra of liposomes (1 mM phospholipid) with C60 (a) or a cationic derivative of...
Figure 4: Fluorescence spectra of 1-pyrenebutyric acid (PyBA) in cationic derivative of C60 (catC60)-loaded l...
Figure 5: Photoinduced generation of reactive oxygen species (ROS) by cationic derivative of C60 (catC60)-loa...
Beilstein J. Org. Chem. 2024, 20, 2722–2731, doi:10.3762/bjoc.20.230
Graphical Abstract
Figure 1: Selected natural products containing spiro-indolenines.
Scheme 1: Synthesis of spiro[indole-heterocycles].
Scheme 2: Synthetic strategy for the new synthesis of 2,3-diaminoindolenines [21] and spiro[indole-isoquinolines]....
Scheme 3: Scope of the synthesis of spiro[indole-THIQs]. aα-aminoamidine 2b has been isolated (54%) too; bα-a...
Scheme 4: Two-step synthesis using p-methylaniline.
Scheme 5: Investigation of the one-pot four-step synthetic protocol employing N-Ph-benzoxazepine 5.
Figure 2: Time profile of the reaction of N-Ph-THIQ, 3,5-dimethoxyaniline and t-BuNC conducted under optimize...
Scheme 6: Proposed mechanism.
Beilstein J. Org. Chem. 2024, 20, 2708–2719, doi:10.3762/bjoc.20.228
Graphical Abstract
Figure 1: Synthesis of uracil-based alkynes and aryl structures [51,62-65].
Figure 2: Structures of uracil derivatives A, B, and C.
Scheme 1: Strategy for the synthesis of the cyclised product 5. Conditions: i) Br2 (2 equiv), Ac2O (1.5 equiv...
Scheme 2: Synthesis and isolated yields of 1,3-dimethyl-5-aryl-6-[2-(aryl)ethynyl]uracils 4a–i. Reaction cond...
Scheme 3: Scope and isolated yields of the synthesis of 5. Reaction conditions: 4 (1 equiv), p-TsOH·H2O (20 e...
Scheme 4: Proposed reaction mechanism of the cyclisation with N,N-dimethylanilino functional groups.
Figure 3: UV–vis absorption (left) and emission (right, λex = 400 nm) spectra of 5a, 5d, 5f, 5g, 5h, and 5i i...
Beilstein J. Org. Chem. 2024, 20, 1988–2004, doi:10.3762/bjoc.20.175
Graphical Abstract
Scheme 1: Synthesis of triazolopyridinium salts [34-36].
Scheme 2: Synthesis of pyrazoles [37].
Scheme 3: Synthesis of indazoles from ketone-derived hydrazones [38].
Scheme 4: Intramolecular C(sp2)–H functionalization of aldehyde-derived N-(2-pyridinyl)hydrazones for the syn...
Scheme 5: Synthesis of pyrazolo[4,3-c]quinoline derivatives [40].
Scheme 6: Synthesis of 1,3,4-oxadiazoles and Δ3-1,3,4-oxadiazolines [41].
Scheme 7: Synthesis of 1,3,4-oxadiazoles [43].
Scheme 8: Synthesis of 2-(1,3,4-oxadiazol-2-yl)anilines [44].
Scheme 9: Synthesis of fused s-triazolo perchlorates [45].
Scheme 10: Synthesis of 1-aryl and 1,5-disubstitued 1,2,4-triazoles [49].
Scheme 11: Synthesis of 1,3,5-trisubstituted 1,2,4-triazoles [50].
Scheme 12: Alternative synthesis of 1,3,5-trisubstituted 1,2,4-triazoles [51].
Scheme 13: Synthesis of 5-amino 1,2,4-triazoles [55].
Scheme 14: Synthesis of 1-arylpyrazolines [58].
Scheme 15: Synthesis of 3‑aminopyrazoles [60].
Scheme 16: Synthesis of [1,2,4]triazolo[4,3-a]quinolines [61].·
Scheme 17: Synthesis of 1,2,3-thiadiazoles [64].
Scheme 18: Synthesis of 5-thioxo-1,2,4-triazolium inner salts [65].
Scheme 19: Synthesis of 1-aminotetrazoles [66].
Scheme 20: C(sp2)–H functionalization of aldehyde-derived hydrazones: general mechanisms.
Scheme 21: C(sp2)–H functionalization of benzaldehyde diphenyl hydrazone [68,69].
Scheme 22: Phosphorylation of aldehyde-derived hydrazones [70].
Scheme 23: Azolation of aldehyde-derived hydrazones [72].
Scheme 24: Thiocyanation of benzaldehyde-derived hydrazone 122 [73].
Scheme 25: Sulfonylation of aromatic aldehyde-derived hydrazones [74].
Scheme 26: Trifluoromethylation of aromatic aldehyde-derived hydrazones [76].
Scheme 27: Electrooxidation of benzophenone hydrazones [77].
Scheme 28: Electrooxidative coupling of benzophenone hydrazones and alkenes [77].
Scheme 29: Electrosynthesis of α-diazoketones [78].
Scheme 30: Electrosynthesis of stable diazo compounds [80].
Scheme 31: Photoelectrochemical synthesis of alkenes through in situ generation of diazo compounds [81].
Scheme 32: Synthesis of nitriles [82].
Scheme 33: Electrochemical oxidation of ketone-derived NH-allylhydrazone [83].
Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162
Graphical Abstract
Scheme 1: Mechanism of the GBB reaction.
Scheme 2: Comparison of the performance of Sc(OTf)3 with some RE(OTf)3 in a model GBB reaction. Conditions: a...
Scheme 3: Comparison of the performance of various Brønsted acid catalysts in the synthesis of GBB adduct 6. ...
Scheme 4: Synthesis of Brønsted acidic ionic liquid catalyst 7. Conditions: a) neat, 60 °C, 24 h; b) TfOH, DC...
Scheme 5: Aryliodonium derivatives as organic catalysts in the GBB reaction. In the box the proposed binding ...
Scheme 6: DNA-encoded GBB reaction in micelles made of amphiphilic polymer 13. Conditions: a) 13 (50 equiv), ...
Scheme 7: GBB reaction catalyzed by cyclodextrin derivative 14. Conditions: a) 14 (1 mol %), water, 100 °C, 4...
Scheme 8: Proposed mode of activation of CALB. a) activation of the substrates; b) activation of the imine; c...
Scheme 9: One-pot GBB reaction–Suzuki coupling with a bifunctional hybrid biocatalyst. Conditions: a) Pd(0)-C...
Scheme 10: GBB reaction employing 5-HMF (23) as carbonyl component. Conditions: a) TFA (20 mol %), EtOH, 60 °C...
Scheme 11: GBB reaction with β-C-glucopyranosyl aldehyde 26. Conditions: a) InCl3 (20 mol %), MeOH, 70 °C, 2–3...
Scheme 12: GBB reaction with diacetylated 5-formyldeoxyuridine 29, followed by deacetylation of GBB adduct 30....
Scheme 13: GBB reaction with glycal aldehydes 32. Conditions: a) HFIP, 25 °C, 2–4 h.
Scheme 14: Vilsmeier–Haack formylation of 6-β-acetoxyvouacapane (34) and subsequent GBB reaction. Conditions: ...
Scheme 15: GBB reaction of 4-formlyl-PCP 37. Conditions: a) HOAc or HClO4, MeOH/DCM (2:3), rt, 3 d.
Scheme 16: GBB reaction with HexT-aldehyde 39. Conditions: a) 39 (20 nmol) and amidine (20 μmol), MeOH, rt, 6 ...
Scheme 17: GBB reaction of 2,4-diaminopirimidine 41. Conditions: a) Sc(OTf)3 (20 mol %), MeCN, 120 °C (MW), 1 ...
Scheme 18: Synthesis of N-edited guanine derivatives from 3,6-diamine-1,2,4-triazin-5-one 44. Conditions: a) S...
Scheme 19: Synthesis of 2-aminoimidazoles 49 by a Mannich-3CR followed by a one-pot intramolecular oxidative a...
Scheme 20: On DNA Suzuki–Miyaura reaction followed by GBB reaction. Conditions: a) CsOH, sSPhos-Pd-G2; b) AcOH...
Scheme 21: One-pot cascade synthesis of 5-iminoimidazoles. Conditions: a) Na2SO4, DMF, 220 °C (MW).
Scheme 22: GBB reaction of 5-amino-1H-imidazole-4-carbonile 57. Conditions: a) HClO4 (5 mol %), MeOH, rt, 24 h....
Scheme 23: One-pot cascade synthesis of indole-imidazo[1,2,a]pyridine hybrids. In blue the structural motif in...
Scheme 24: One-pot cascade synthesis of fused polycyclic indoles 67 or 69 from indole-3-carbaldehyde. Conditio...
Scheme 25: One-pot cascade synthesis of linked- and bridged polycyclic indoles from indole-2-carbaldehyde (70)...
Scheme 26: One-pot cascade synthesis of pentacyclic dihydroisoquinolines (X = N or CH). In blue the structural...
Scheme 27: One-pot stepwise synthesis of imidazopyridine-fused benzodiazepines 85. Conditions: a) p-TsOH (20 m...
Scheme 28: One-pot stepwise synthesis of benzoxazepinium-fused imidazothiazoles 89. Conditions: a) Yb(OTf)3 (2...
Scheme 29: One-pot stepwise synthesis of fused imidazo[4,5,b]pyridines 95. Conditions: a) HClO4, MeOH, rt, ove...
Scheme 30: Synthesis of heterocyclic polymers via the GBB reaction. Conditions: a) p-TsOH, EtOH, 70 °C, 24 h.
Scheme 31: One-pot multicomponent reaction towards the synthesis of covalent organic frameworks via the GBB re...
Scheme 32: One-pot multicomponent reaction towards the synthesis of covalent organic frameworks via the GBB re...
Scheme 33: GBB-like multicomponent reaction towards the synthesis of benzothiazolpyrroles (X = S) and benzoxaz...
Scheme 34: GBB-like multicomponent reaction towards the formation of imidazo[1,2,a]pyridines. Conditions: a) I2...
Scheme 35: Post-functionalization of GBB products via Ugi reaction. Conditions a) HClO4, DMF, rt, 24 h; b) MeO...
Scheme 36: Post-functionalization of GBB products via Click reaction. Conditions: a) solvent-free, 150 °C, 24 ...
Scheme 37: Post-functionalization of GBB products via cascade alkyne–allene isomerization–intramolecular nucle...
Scheme 38: Post-functionalization of GBB products via metal-catalyzed intramolecular N-arylation. In red and b...
Scheme 39: Post-functionalization of GBB products via isocyanide insertion (X = N or CH). Conditions: a) HClO4...
Scheme 40: Post-functionalization of GBB products via intramolecular nucleophilic addition to nitriles. Condit...
Scheme 41: Post-functionalization of GBB products via Pictet–Spengler cyclization. Conditions: a) 4 N HCl/diox...
Scheme 42: Post-functionalization of GBB products via O-alkylation. Conditions: a) TFA (20 mol %), EtOH, 120 °...
Scheme 43: Post-functionalization of GBB products via macrocyclization (X = -CH2CH2O-, -CH2-, -(CH2)4-). Condi...
Figure 1: Antibacterial activity of GBB-Ugi adducts 113 on both Gram-negative and Gram-positive strains.
Scheme 44: GBB multicomponent reaction using trimethoprim as the precursor. Conditions: a) Yb(OTf)3 or Y(OTf)3...
Figure 2: Antibacterial activity of GBB adducts 152 against MRSA and VRE; NA = not available.
Figure 3: Antibacterial activity of GBB adduct 153 against Leishmania amazonensis promastigotes and amastigot...
Figure 4: Antiviral and anticancer evaluation of the GBB adducts 154a and 154b. In vitro antiproliferative ac...
Figure 5: Anticancer activity of the GBB-furoxan hybrids 145b, 145c and 145d determined through antiprolifera...
Scheme 45: Synthesis and anticancer activity of the GBB-gossypol conjugates. Conditions: a) Sc(OTf)3 (10 mol %...
Figure 6: Anticancer activity of polyheterocycles 133a and 136a against human neuroblastoma. Clonogenic assay...
Figure 7: Development of GBB-adducts 158a and 158b as PD-L1 antagonists. HTRF assays were carried out against...
Figure 8: Development of imidazo[1,2-a]pyridines and imidazo[1,2-a]pyrazines as TDP1 inhibitors. The SMM meth...
Figure 9: GBB adducts 164a–c as anticancer through in vitro HDACs inhibition assays. Additional cytotoxic ass...
Figure 10: GBB adducts 165, 166a and 166b as anti-inflammatory agents through HDAC6 inhibition; NA = not avail...
Scheme 46: GBB reaction of triphenylamine 167. Conditions: a) NH4Cl (10 mol %), MeOH, 80 °C (MW), 1 h.
Scheme 47: 1) Modified GBB-3CR. Conditions: a) TMSCN (1.0 equiv), Sc(OTf)3 (0.2 equiv), MeOH, 140 °C (MW), 20 ...
Scheme 48: GBB reaction to assemble imidazo-fused heterocycle dimers 172. Conditions: a) Sc(OTf)3 (20 mol %), ...
Figure 11: Model compounds 173 and 174, used to study the acid/base-triggered reversible fluorescence response...
Beilstein J. Org. Chem. 2024, 20, 1348–1375, doi:10.3762/bjoc.20.119
Graphical Abstract
Figure 1: Generation of alkyl and acyl radicals via C–O bond breaking.
Figure 2: General photocatalytic mechanism.
Scheme 1: Photoredox-catalyzed hydroacylation of olefins with aliphatic carboxylic acids.
Scheme 2: Acylation–aromatization of p-quinone methides using carboxylic acids.
Scheme 3: Visible-light-induced deoxygenation–defluorination for the synthesis of γ,γ-difluoroallylic ketones....
Scheme 4: Photochemical hydroacylation of azobenzenes with carboxylic acids.
Scheme 5: Photoredox-catalyzed synthesis of flavonoids.
Scheme 6: Synthesis of O-thiocarbamates and photocatalytic reduction of O-thiocarbamates.
Scheme 7: Deoxygenative borylation of alcohols.
Scheme 8: Trifluoromethylation of O-alkyl thiocarbonyl substrates.
Scheme 9: Redox-neutral radical coupling reactions of alkyl oxalates and Michael acceptors.
Scheme 10: Visible-light-catalyzed and Ni-mediated syn-alkylarylation of alkynes.
Scheme 11: 1,2-Alkylarylation of alkenes with aryl halides and alkyl oxalates.
Scheme 12: Deoxygenative borylation of oxalates.
Scheme 13: Coupling of N-phthalimidoyl oxalates with various acceptors.
Scheme 14: Cross-coupling of O-alkyl xanthates with aryl halides via dual photoredox and nickel catalysis.
Scheme 15: Deoxygenative borylation of secondary alcohol.
Scheme 16: Deoxygenative alkyl radical generation from alcohols under visible-light photoredox conditions.
Scheme 17: Deoxygenative alkylation via alkoxy radicals against hydrogenation or β-fragmentation.
Scheme 18: Direct C–O bond activation of benzyl alcohols.
Scheme 19: Deoxygenative arylation of alcohols using NHC to activate alcohols.
Scheme 20: Deoxygenative conjugate addition of alcohol using NHC as alcohol activator.
Scheme 21: Synthesis of polysubstituted aldehydes.
Beilstein J. Org. Chem. 2024, 20, 1167–1178, doi:10.3762/bjoc.20.99
Graphical Abstract
Figure 1: Examples of different compounds containing the indanone moiety.
Figure 2: Synthesis of unsaturated β-ketoesters (Knoevenagel derivatives). aIsolated yield after purification...
Figure 3: Synthesis of 3-aryl-2-ethoxycarbonyl-1-indanones mediated by bismuth triflate. aIsolated yield afte...
Scheme 1: Previous methods describing decarboxylation reactions of indanones and xanthenones.
Figure 4: Controlled decarboxylation directed by bismuth triflate at 100 °C. Synthesis of 3-aryl-1-indanones. ...
Figure 5: Impact of indanone derivatives on cell viability of tumor cells. Cell viability was determined by M...
Beilstein J. Org. Chem. 2024, 20, 898–911, doi:10.3762/bjoc.20.80
Graphical Abstract
Figure 1: Uracil derivatives in drugs.
Figure 2: Present work as compared to previous studies [25,57-59].
Scheme 1: Synthesis of 1,3-dimethly-5-[2-(aryl)ethynyl]-6-[2-(aryl)ethynyl]uracils 4 and 1,3-dimethyl-5-aryl-...
Scheme 2: Synthesis of 5-bromo-1,3-dimethyl-6-[2-(aryl)ethynyl]uracils 3a–j. Reaction conditions: 2 (1.0 equi...
Scheme 3: Structure of the starting material 2 with its possible mesomeric structures.
Scheme 4: Synthesis of 1,3-dimethyl-5-[2-(aryl)ethynyl]-6-[2-(aryl)ethynyl]uracils 4a–h. Reaction conditions: ...
Scheme 5: Synthesis of 1,3-dimethyl-5-aryl-6-[2-(aryl)ethynyl]uracils 5a–t. Reaction conditions: 3 (1 equiv),...
Figure 3: ORTEP diagram of 5a front view (a) and side view (b). a) Interactions of the molecules within and b...
Figure 4: UV–vis absorption (left) and emission (right, λex = 400 nm) spectra of 1,3-dimethyl-5-phenyl-6-[2-(...
Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45
Graphical Abstract
Figure 1: Principle of switchable molecular tweezers.
Figure 2: Principle of pH-switchable molecular tweezers 1 [19].
Figure 3: a) pH-Switchable tweezers 2 substituted with alkyl chains as switchable lipids. b) Schematic depict...
Figure 4: Modification of spectral properties of 3 by controlled induction of Pt–Pt interactions.
Figure 5: Conformational switching of di(hydroxyphenyl)pyrimidine-based tweezer 4 upon alkylation or fluoride...
Figure 6: Hydrazone-based pH-responsive tweezers 5 for mesogenic modulation.
Figure 7: pH-Switchable molecular tweezers 6 bearing acridinium moieties.
Figure 8: a) Terpyridine and pyridine-hydrazone-pyridine analogs molecular tweezers and b) extended pyridine ...
Figure 9: Terpyridine-based molecular tweezers with M–salphen arms and their field of application. Figure 9 was adapt...
Figure 10: a) Terpyridine-based molecular tweezers for diphosphate recognition [48]; b) bishelicene chiroptical te...
Figure 11: Terpyridine-based molecular tweezers with allosteric cooperative binding.
Figure 12: Terpyridine-based molecular tweezers presenting closed by default conformation.
Figure 13: Pyridine-pyrimidine-pyridine-based molecular tweezers.
Figure 14: Coordination-responsive molecular tweezers based on nitrogen-containing ligands.
Figure 15: Molecular tweezers exploiting the remote bipyridine or pyridine binding to trigger the conformation...
Figure 16: Bipyridine-based molecular tweezers exploiting the direct s-trans to s-cis-switching for a) anion b...
Figure 17: a) Podand-based molecular tweezers [66,67]. b) Application of tweezers 32 for the catalytic allosteric reg...
Figure 18: Anion-triggered molecular tweezers based on calix[4]pyrrole.
Figure 19: Anion-triggered molecular tweezers.
Figure 20: a) Principle of the weak link approach (WLA) developed by Mirkin and its application to b) symmetri...
Figure 21: Molecular tweezers as allosteric catalyst in asymmetric epoxide opening [80].
Figure 22: Allosteric regulation of catalytic activity in ring-opening polymerization with double tweezers 41.
Figure 23: a) Conformational switching of 42 by intramolecular –S–S– bridge formation. b) Shift of conformatio...
Figure 24: a) Redox-active glycoluril-TTF tweezers 44. b) Mechanism of stepwise oxidation of said tweezers wit...
Figure 25: Mechanism of formation of the mixed-valence dimers of tweezers 45.
Figure 26: Mechanism of carbohydrate liberation upon redox-mediated conformation switching of 46.
Figure 27: a) The encapsulation properties of 47 as well as the DCTNF release process from its host–guest comp...
Figure 28: Redox-active bipyridinium-based tweezers. a) With a ferrocenyl hinge 49, b) with a propyl hinge 50 ...
Figure 29: Redox-active calix[4]arene porphyrin molecular tweezers.
Figure 30: a) Mechanism of the three orthogonal stimuli. b) Cubic scheme showing the eight different states of ...
Figure 31: Redox-controlled molecular gripper based on a diquinone resorcin[4]arene.
Figure 32: a) Shinkai's butterfly tweezers and their different host–guest properties depending on the isomer. ...
Figure 33: Cyclam-tethered tweezers and their different host–guest complexes depending on their configuration.
Figure 34: Azobenzene-based catalytic tweezers.
Figure 35: Photoswitchable PIEZO channel mimic.
Figure 36: Stilbene-based porphyrin tweezers for fullerene recognition.
Figure 37: Stiff-stilbene-based tweezers with urea or thiourea functional units for a) anion binding, b) anion...
Figure 38: Feringa’s photoswitchable organocatalyst (a) and different catalyzed reactions with that system (b)....
Figure 39: a) Irie and Takeshita’s thioindigo-based molecular tweezers. b) Family of hemithioindigo-based mole...
Figure 40: Dithienylethylene crown ether-bearing molecular tweezers reported by Irie and co-workers.
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, 346–378, doi:10.3762/bjoc.20.35
Graphical Abstract
Scheme 1: Comparison between Barton and NHPI ester radical precursors.
Scheme 2: Overview of the mechanisms and activation modes involved in radical generation from RAEs.
Scheme 3: Common mechanisms in photocatalysis.
Scheme 4: A) Giese-type radical addition of NHPI esters mediated by a reductive quenching photocatalytic cycl...
Scheme 5: A) Minisci-type radical addition of NHPI esters. B) Reaction mechanism involving an “off-cycle” red...
Scheme 6: Activation of NHPI esters through hydrogen-bonding in an oxidative quenching photocatalytic cycle.
Scheme 7: SET activation of RAE facilitated by a Lewis acid catalyst.
Scheme 8: PCET activation of NHPI esters in the context of a radical-redox annulation.
Scheme 9: Activation enabled by a strong excited-state reductant catalyst and its application in the dearomat...
Scheme 10: Proposed formation of an intramolecular charge-transfer complex in the synthesis of (spiro)anellate...
Scheme 11: Formation of a charge-transfer complex between enamides and NHPI esters enabled by a chiral phospha...
Scheme 12: Activation of NHPI ester through the formation of photoactive EDA-complexes.
Scheme 13: A) EDA complex-mediated radical hydroalkylation reactions of NHPI esters. B) Proposed mechanism for...
Scheme 14: Proposed radical chain mechanism initiated by EDA-complex formation.
Scheme 15: A) Photoinduced decarboxylative borylation. B) Proposed radical chain mechanism.
Scheme 16: A) Activation of NHPI esters mediated by PPh3/NaI. B) Proposed catalytic cycle involving EDA-comple...
Scheme 17: A) Radical generation facilitated by EDA complex formation between PTH1 catalyst and NHPI esters. B...
Scheme 18: Proposed catalytic cycle for the difunctionalization of styrenes.
Scheme 19: Formation of a charge-transfer complex between NHPI esters and Cs2CO3 enables decarboxylative amina...
Scheme 20: 3-Acetoxyquinuclidine as catalytic donor in the activation of TCNHPI esters.
Scheme 21: A) Photoinduced Cu-catalyzed decarboxylative amination. B) Proposed catalytic cycle. C) Radical clo...
Scheme 22: A) Photoinduced Pd-catalyzed aminoalkylation of 1,4-dienes. B) Proposed catalytic cycle.
Scheme 23: A) TM-catalyzed decarboxylative coupling of NHPI esters and organometallic reagents. B) Representat...
Scheme 24: Synthetic applications of the TM-catalyzed decarboxylative coupling of NHPI esters and organometall...
Scheme 25: A) Ni-catalyzed cross-electrophile coupling of NHPI esters. B) Representative catalytic cycle.
Scheme 26: A) Synthetic applications of decarboxylative cross-electrophile couplings. B) Decarboxylative aryla...
Scheme 27: A) Activation of tetrachlorophthalimide redox-active esters enabled by a low-valency Bi complex. B)...
Scheme 28: Activation of NHPI esters mediated by Zn0 applied in a Z-selective alkenylation reaction.
Scheme 29: A) Activation of NHPI esters enabled by a pyridine-boryl radical species applied to the decarboxyla...
Scheme 30: A) Decarboxylative coupling of RAE and aldehydes enabled by NHC-catalyzed radical relay. B) Propose...
Scheme 31: A) Decarboxylative C(sp3)–heteroatom coupling reaction of NHPI esters under NHC catalysis B) The NH...
Scheme 32: A) Electrochemical Giese-type radical addition of NHPI esters. B) Reaction mechanism.
Scheme 33: Electrochemical Minisci-type radical addition of NHPI-esters.
Scheme 34: Ni-electrocatalytic cross-electrophile coupling of NHPI esters with aryl iodides.
Scheme 35: A) Decarboxylative arylation of NHPI esters under Ag-Ni electrocatalysis B) Formation of AgNP on th...
Scheme 36: Synthetic applications of decarboxylative couplings of NHPI esters under Ni-electrocatalysis.
Scheme 37: Examples of natural product syntheses in which RAEs were used in key C–C bond forming reactions.
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. 2024, 20, 118–124, doi:10.3762/bjoc.20.12
Graphical Abstract
Figure 1: Representative dihydropyrido[1,2-a]indolone derivatives.
Scheme 1: Selected works for the construction of dihydropyrido[1,2-a]indolones and current methodology.
Scheme 2: Substrate scope of the cascade reaction.
Scheme 3: Radical trapping experiment.
Figure 2: UV–vis spectra of substrates; [1a] 0.33 M, [2a] 0.11 M.
Scheme 4: Plausible reaction mechanism.
Beilstein J. Org. Chem. 2023, 19, 1867–1880, doi:10.3762/bjoc.19.139
Graphical Abstract
Figure 1: Chemical structures of pyridine-3,5-dicarbonitrile-based TADF emitters.
Scheme 1: Synthesis of dicyanocarbazole 6. Reaction conditions: a) cyanoacetamide, piperidine, methanol, 40 °...
Scheme 2: Synthesis of dicyanocarbazoles 7–9. Reaction conditions: a) corresponding ethynyl arene, Pd(Ph3P)4 ...
Figure 2: Absorption (a, b) and PL (c, d) spectra of dilute toluene, THF, and chloroform solutions (10−5 M) a...
Figure 3: PL spectra (a) and PL decay curves (b) of air-equilibrated (as prepared) and deoxygenated toluene s...
Figure 4: Non-normalized (a) and normalized (b) PL spectra and PL decay curves (c) of the film of a 10 wt % m...
Figure 5: TGA (a) and DSC 2nd heating (b) curves of compounds 6–9.
Figure 6: CV curves of compounds 6–9.
Figure 7: Photoelectron emission spectra of the vacuum-deposited films of compounds 6–9 on glass substrates c...
Figure 8: The current transients (a) for electrons recorded at the different voltages for the vacuum-deposite...
Beilstein J. Org. Chem. 2023, 19, 1858–1866, doi:10.3762/bjoc.19.138
Graphical Abstract
Scheme 1: Reaction of the La@C2v-C82 anion with benzyl bromide derivatives.
Figure 1: Changes in absorption spectra during the reaction of La@C2v-C82 anion with 1a.
Figure 2: HPLC profiles of the reaction mixture. Conditions: Buckyprep column (⌀ = 4.6 × 250 mm); eluent, tol...
Figure 3: HPLC profiles (Buckyprep column (⌀ = 4.6 × 250 mm); eluent, toluene; flow rate, 1.0 mL/min; UV dete...
Figure 4: Absorption spectra of 2, 3, 4, and 5 in CS2 and absorption spectra of C14, C10, C18, and C9 in Ce@C2...
Figure 5: ORTEP drawing of 3a with thermal ellipsoids shown at 50% probability level. Only an independent uni...
Figure 6: (a) Charge density of La@C2v-C82 anion as a function of its POAV values and (b) an enlarged part vi...
Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131
Graphical Abstract
Scheme 1: Photocatalytic decarboxylative transformations mediated by the NaI/PPh3 catalyst system.
Scheme 2: Proposed catalytic cycle of NaI/PPh3 photoredox catalysis.
Scheme 3: Decarboxylative alkenylation of redox-active esters by NaI/PPh3 catalysis.
Scheme 4: Decarboxylative alkenylation mediated by NaI/PPh3 catalysis.
Scheme 5: NaI-mediated photoinduced α-alkenylation of Katritzky salts 7.
Scheme 6: n-Bu4NI-mediated photoinduced decarboxylative olefination.
Scheme 7: Proposed mechanism of the n-Bu4NI-mediated photoinduced decarboxylative olefination.
Scheme 8: Photodecarboxylative alkylation of redox-active esters with diazirines.
Scheme 9: Photoinduced iodine-anion-catalyzed decarboxylative/deaminative C–H alkylation of enamides.
Scheme 10: Photocatalytic C–H alkylation of coumarins mediated by NaI/PPh3 catalysis.
Scheme 11: Photoredox alkylation of aldimines by NaI/PPh3 catalysis.
Scheme 12: Photoredox C–H alkylation employing ammonium iodide.
Scheme 13: NaI/PPh3/CuBr cooperative catalysis for photocatalytic C(sp3)–O/N cross-coupling reactions.
Scheme 14: Proposed mechanism of NaI/PPh3/CuBr cooperative catalysis for photocatalytic C(sp3)–O/N cross-coupl...
Scheme 15: Photocatalytic decarboxylative [3 + 2]/[4 + 2] annulation between enynals and γ,σ-unsaturated N-(ac...
Scheme 16: Proposed mechanism for the decarboxylative [3 + 2]/[4 + 2] annulation.
Scheme 17: Decarboxylative cascade annulation of alkenes/1,6-enynes with N-hydroxyphthalimide esters.
Scheme 18: Decarboxylative radical cascade cyclization of N-arylacrylamides.
Scheme 19: NaI/PPh3-driven photocatalytic decarboxylative radical cascade alkylarylation.
Scheme 20: Proposed mechanism of the NaI/PPh3-driven photocatalytic decarboxylative radical cascade cyclizatio...
Scheme 21: Visible-light-promoted decarboxylative cyclization of vinylcycloalkanes.
Scheme 22: NaI/PPh3-mediated photochemical reduction and amination of nitroarenes.
Scheme 23: PPh3-catalyzed alkylative iododecarboxylation with LiI.
Scheme 24: Visible-light-triggered iodination facilitated by N-heterocyclic carbenes.
Scheme 25: Visible-light-induced photolysis of phosphonium iodide salts for monofluoromethylation.
Beilstein J. Org. Chem. 2023, 19, 1766–1775, doi:10.3762/bjoc.19.129
Graphical Abstract
Figure 1: Chemical structures of the molecular components used in this work: Co(II) complex 1 as the novel ca...
Figure 2: ORTEP drawing of crystal polymorph 1a (left) and 1b (right), shown at the 50% probability level. Hy...
Figure 3: UV–vis absorbance of complex 1 in DMA. Inset: zoom-in of the 500–800 nm range to visualize the low-...
Figure 4: Cyclic voltammetry of complex 1 in 0.1 M TBAPF6 solution of (a) DMA and (b) DMA/TEOA 5:1 (v/v). Bla...
Figure 5: Time evolution of CO (blue squares) and H2 (red triangles) with the power functional fitting (blue ...
Scheme 1: Proposed mechanism for the photoinduced reduction of carbon dioxide with the system presented in th...