Photocatalyst-free H₂O-regulated and regiodivergent multicomponent hydrogenation/bifunctional sulfonylation of alkynes

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(6), P. 3301 - 3307

Published: Jan. 1, 2024

An efficient multicomponent reaction for the preparation of vinyl sulfone was achieved by hydrogenation/bifunctional sulfonylation alkynyl esters with N- allyl bromodifluoroacetamide, DABSO, and H 2 O under visible-light-only conditions.

Language: Английский

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Photochemical difluoromethylation of alkynes: synthesis of CF₂H-substituted seven-membered dioxodibenzothiazepines and dibenzazepines

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(8), P. 1968 - 1974

Published: Jan. 1, 2023

A general and efficient photochemical strategy for difluoromethylation/radical cascade cyclization of alkynes with sodium difluoromethylsulfinate (NaSO 2 CF H) has been disclosed.

Language: Английский

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Recent advancements in metal‐catalyst‐free multicomponent radical sulfonylation of alkynes

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(43)

Published: June 4, 2024

Vinyl sulfones are crucial building blocks in synthetic chemistry and core structural units of pharmaceutically active molecules, thus extensive investigations have been conducted on the construction these skeletons. In contrast to classical approaches, radical sulfonylation alkynes for producing vinyl has garnered considerable interest because its mild conditions high efficiency. Radical sulfonation typically begins with sulfonyl attacking alkynes, followed by further functionalization. Moreover, association metal-catalyst-free systems multicomponent reactions (MCRs) offers an environmentally friendly pathway efficiently constructing complex scaffolds from readily available partners. However, there is no comprehensive review summarizing advancements alkynes. Hence, we provide a categorical overview based objects (hydrosulfonylation, carbosulfonylation, aminosulfonylation, oxysulfonylation, sulfosulfonylation, selenosulfonylation, iodosulfonylation), along interpretations reaction mechanisms.

Language: Английский

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Recent Progress in C–S Bond Formation via Electron Donor-Acceptor Photoactivation

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review summarizes recent progress in EDA complex-promoted C–S bond formation using various sulfur-containing substrates under mild conditions via visible light irradiation.

Language: Английский

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Photoinduced tandem radical cyclization/heteroarylation of N-allylbromodifluoroacetamides with quinoxalin-2(1H)-ones or coumarins under metal- and photocatalyst-free conditions

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(22), P. 10744 - 10750

Published: Jan. 1, 2023

A photocatalyst-free visible-light-promoted tandem intramolecular cyclization/heteroarylation between bromodifluoroacetamides and quinoxalin-2(1 H )-ones or coumarins was developed. The process could generate a broad range of α , -difluoro-γ-lactams.

Language: Английский

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Visible light driven multicomponent synthesis of difluoroamidosulfonyl quinoline derivatives

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 21(4), P. 846 - 850

Published: Dec. 24, 2022

A visible-light-induced photocatalyst-free three-component radical tandem cyclization of N-propargylamine and N-allylbromodifluoroacetamides with the insertion sulfur dioxide has been developed. Diverse difluoroamidosulfonylated quinolines are obtained in moderate to good yields. This protocol features broad functional group tolerance high regioselectivity. Moreover, mechanistic studies reveal involvement pathway formation an electron donor-acceptor (EDA) complex this reaction.

Language: Английский

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Recent Progress on the Synthesis of Benzazepine Derivatives via Radical Cascade Cyclization Reactions

Chinese Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 42(12), P. 3979 - 3979

Published: Jan. 1, 2022

Language: Английский

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Visible Light‐Induced EDA‐Complex Triggered Annulative Difunctionalization via Olefin‐Olefin Coupling and Radical Truce‐Smiles Rearrangement

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(1), P. 148 - 153

Published: Dec. 9, 2023

Abstract An EDA complex comprising N ‐allyl bromodifluoroacetamides and tertiary alkyl amine was exploited to facilitate annulative difunctionalization reaction under visible‐light irradiation. This external photocatalyst‐free methodology garners olefin‐olefin coupling featuring a radical Truce‐Smiles rearrangement produced long‐chain functionalized gem ‐difluoropyrrolidones from N‐ substituted methacryloyl sulfonamides, while simple ‐aryl methacrylamides furnished pyrrolidinone‐oxindole hybrid lactams in high yields. Mechanistic investigations substantiate combined mechanism, involving charge‐transfer complex‐based cascade, alongside an α‐aminoalkyl radical‐triggered XAT process, exhibiting quantum yield value of 1.48.

Language: Английский

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NHC Catalyzed Radical Tandem Cyclization: An Efficient Synthesis of α,α-Difluoro-γ-lactam Derivatives

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(34), P. 6988 - 6998

Published: Jan. 1, 2024

Herein, an N-heterocyclic carbene (NHC) catalyzed radical tandem cyclization reaction of

Language: Английский

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Visible light-promoted intermolecular cyclization/aromatization of chalcones and 2-mercaptobenzimidazolesviaan EDA complex and a mechanism study

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(25), P. 5139 - 5144

Published: Jan. 1, 2022

An efficient visible-light-promoted intermolecular cyclization and aromatization approach was developed for the synthesis of abundant benzimidazo[2,1- b ]thiazoles via an EDA complex.

Language: Английский

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