Paired Electrolysis-Enabled Arylation of Quinoxalin-2(1H)-ones

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(9), P. 6117 - 6125

Published: April 24, 2024

The first paired electrolysis-enabled arylation of quinoxalin-2(1H)-ones was achieved using cyanoarenes as the reagents. A variety 3-arylquinoxalin-2(1H)-ones with various important functional groups were obtained in moderate to good yields under metal- and chemical oxidant-free conditions. With a pair reductive oxidative processes occurring among substrates reaction intermediates, power consumption can be dramatically reduced.

Language: Английский

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(Indol-3-yl)(DMIX)Iodonium Salts: Novel Electrophilic Indole Reagents

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3189 - 3194

Published: April 8, 2024

A new umpolung approach to the C3–H functionalization of indoles with diverse nucleophiles based on intermediate formation I(III) reagents is described. The 3,5-dimethylisoxazol-4-yl auxiliary allows for selective indole transfer under catalyst-free conditions, which was impossible using previously reported reagents. Combining mildness transition-metal-free conditions and high reactivity hypervalent iodine reagents, this protocol tolerates various functional groups provides access that are difficult prepare conventionally.

Language: Английский

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Transition Metal and Photocatalyst Free Arylation via Photoexcitable Electron Donor Acceptor Complexes:Mediation and Catalysis

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(11)

Published: Jan. 15, 2024

Abstract Visible‐light‐activated organic reactions unlock novel avenues for complex molecular transformations, impossible under standard “thermal” conditions, which makes them powerful tools in the arsenal of synthetic chemistry. However, transition metal‐based or photoredox catalysts are often used to ensure productive absorption visible light, might be not desirable medicinal chemistry and industry due toxicity, low sustainability, high cost most photocatalysts. A more environmentally economically benign approach is based on formation transient electron donor‐acceptor (EDA) complexes between two reagents a reagent an additive, that readily absorb acting as internal photosensitizers. Within EDA complex‐based arylation strategies, chemical transformations mediated by noncovalent interaction molecules, namely electron‐poor aryl halides their equivalents electron‐rich nucleophilic additives. Moreover, besides stoichiometric organocatalysis can achieved certain cases through regeneration donor molecules course reaction. Photoexcitation induces single transfer (SET) process generate radical species step. This Review will focus state‐of‐the‐art strategies utilizing halides, aryldiazonium, diaryliodonium, arylsulfonium arylphosphonium salts reactants, published mainly last five years.

Language: Английский

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Visible‐light Induced C‐3 Carbamoylation of Quinoxalinones Assisted by EDA Complex

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: June 13, 2024

Abstract A visible‐light‐promoted strategy for the decarboxylative C‐3 carbamoylation of quinoxalinone scaffolds is developed. This approach initiates through formation an EDA complex between oxamic acid and quinoxalinone. Successive SET construct C−C bond. method utilizes aerial oxygen as green oxidant eradicates process from use external photocatalysts transition metals. Detailed synthetic photophysical studies enlighten reaction pathway.

Language: Английский

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Visible Light-Induced Electron–Donor–Acceptor-Mediated C-3 Coupling of Quinoxalin-2(1H)-ones with Unactivated Aryl Iodides

Organic Letters, Journal Year: 2024, Volume and Issue: 26(30), P. 6471 - 6476

Published: July 23, 2024

Visible light-induced C-3 arylation of quinoxalin-2(1

Language: Английский

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Photoinduced Metal‐/Additive‐Free Difluoromethylation of N‐Heteroaromatics^†

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 16, 2025

Comprehensive Summary Herein, we report a photo‐induced, metal‐/additive‐free protocol for the difluoromethylation of N ‐heteroaromatics with [bis(difluoroacetoxy)iodo]benzene as reagent. The affords difluoromethylated in moderate to good yield (up 91%). transformation is compatible wide range substrates and has tolerance towards various functional groups. Moreover, synthetic value this method further demonstrated by applications gram‐scale synthesis late‐stage functionalization biologically important molecules.

Language: Английский

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Photoinduced Vicinal Difunctionalization of Diaryliodonium Salts To Access Bis(tetraphenylphosphonium) Salts

Organic Letters, Journal Year: 2025, Volume and Issue: 27(4), P. 1012 - 1017

Published: Jan. 21, 2025

Vicinal bis(tetraarylphosphonium) salts have scarcely been reported in the literature. In this study, we demonstrate that visible-light-induced difunctionalization of ortho-trifluoromethylsulfonylated diaryliodonium conveniently furnishes bis(phosphonium) without additional catalysts or photoinitiators. The methodology establishes a practical platform for preparation using readily available tertiary phosphines. are anticipated to garner great deal interest catalytic and medicinal chemistry.

Language: Английский

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Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations

Chemical Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: March 7, 2025

Constructing chemical bonds under green sustainable conditions has drawn attention from environmental and economic perspectives. The dissociation of (hetero)aryl-halide is a crucial step most arylations affording (hetero)arene derivatives. Herein, we summarize the (hetero)aryl halides activation enabling direct (hetero)arylation trapping reagents construction highly functionalized (hetero)arenes benign conditions. strategies for aryl iodides are classified into (a) hypervalent iodoarene followed by functionalization thermal/photochemical conditions, (b) aryl-I bond in presence bases with/without organic catalysts promoters, (c) photoinduced presence/absence organophotocatalysts, (d) electrochemical direct/indirect electrolysis mediated organocatalysts mediators acting as electron shuttles, (e) electrophotochemical redox-active organocatalysts. These modes result exhibiting diverse reactivity formal cations/radicals/anions aryne precursors. coupling these reactive intermediates with leads to facile selective formation C-C C-heteroatom bonds. ecofriendly, inexpensive, functional group-tolerant offer alternatives transition metal-based catalysis.

Language: Английский

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Arylation of Heterocycles Enabled by Photocatalysis

Topics in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

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Synthesis of Nonclassical Heteroaryl C-Glycosides via Decarboxylative C–H Glycosylation

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10112 - 10126

Published: July 3, 2024

A photoredox-promoted decarboxylative C-H glycosylation for the synthesis of nonclassical heteroaryl C-glycosides is reported. This methodology characterized by an exceedingly simple reaction system, high diastereoselectivity, and good functional group tolerance. Moreover, operational procedure simple, gram-scale highlights practical applicability this protocol.

Language: Английский

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