Visible-light-promoted thioetherification of aryl diazonium salts with thiols via electron donor-acceptor complexes DOI

Zhou Jiang,

Ke You,

Haibo Wu

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 572, P. 114801 - 114801

Published: Dec. 28, 2024

Language: Английский

Photochemical Halogen-Bonding Promoted Synthesis of Vinyl Sulfones via Vinyl and Sulfonyl Radicals DOI

Zhou Jiang,

Ke You,

Haibo Wu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(3), P. 636 - 641

Published: Jan. 10, 2024

A photochemical halogen-bonding-assisted synthesis of vinyl sulfones via radical–radical cross-coupling bromines and sodium sulfinates is developed. This methodology offers a facile efficient approach to various with excellent functional group tolerance under metal-, photocatalyst-, base-, oxidant-free conditions. The reaction also applicable for the late-stage functionalization drug molecules hectogram scale. Moreover, instead sulfites being prepared, these reactions could be conducted using sulfonyl chlorides in one-pot method.

Language: Английский

Citations

13

Electron Donor–Acceptor Complex Enabled Cyclization/Sulfonylation Cascade of N-Heterocycles with Thianthrenium Salts DOI

Zhengjun He,

Zhi Li,

Shuo Lai

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6652 - 6657

Published: July 26, 2024

We report a visible-light-promoted cyclization/sulfonylation cascade of N-heterocycles with thianthrenium salts using DABSO as the SO2 surrogate. This method features excellent functional group tolerance, wide substrate scope, and late-stage elaboration bioactive relevant molecules. Mechanistic investigations reveal that photoactive electron donor–acceptor (EDA) complexes between DABCO are capable generation aryl radicals, which induce following insertion by attacking DABSO, thus triggering key radical cyclization step.

Language: Английский

Citations

9

A radical Smiles rearrangement difunctionalization of activated alkenes via desulfonylation and insertion of sulfur dioxide relay strategy DOI

Si‐Wei Tian,

Zhentao Luo,

Biquan Xiong

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(11), P. 6774 - 6778

Published: Jan. 1, 2024

A novel and attractive photochemical difunctionalization of N -tosyl acrylamide for constructing alkylsulfonylated oxindoles amides with excellent substrate adaptability via a radical Smiles rearrangement strategy is described.

Language: Английский

Citations

7

Deep eutectic solvents as sustainable media for multicomponent sulfonylation: an efficient strategy to synthesize (hetero)aryl sulfones DOI
Haibo Zhu, Yangbo Zhong,

Liyuan Yan

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(3), P. 1387 - 1392

Published: Jan. 1, 2024

A green and sustainable multicomponent sulfonylation starting from boronic acids, K 2 S O 5 halides has been developed using a deep eutectic solvent (DES) as reaction medium.

Language: Английский

Citations

5

Recent advancements in metal‐catalyst‐free multicomponent radical sulfonylation of alkynes DOI
Rongnan Yi, Qiang Li, Hongxin Liu

et al.

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

Citations

5

Recent Progress in C–S Bond Formation via Electron Donor-Acceptor Photoactivation DOI
Sichang Wang, Liting Wang, Jin Cui

et al.

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

Citations

0

Radical-mediated sulfonylation relay of alkyl alkynes/alkenes and electron-deficient alkenes to access vinyl and alkyl sulfones DOI
Jinhui Liu,

Fang Long,

Qing Li

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A radical-mediated sulfonylation relay of alkyl alkynes/alkenes with electron-deficient alkenes using Na 2 S O 4 as a linker is developed to synthesize highly selective ( Z )-vinyl and sulfones under metal-free catalyzed system.

Language: Английский

Citations

0

Alkylsulfonylation of alkenes involving copper carbene coupling: access to alkyl–alkyl sulfones DOI

Chuan‐Chong Peng,

Fang Long,

Rui Feng

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 1975 - 1981

Published: Jan. 1, 2024

A novel alkyl radical-initiated alkylsulfonylation of alkenes involving copper carbene coupling is developed for the synthesis various alkyl–alkyl sulfones by employing potassium metabisulphite (K 2 S O 5 ) as a connector.

Language: Английский

Citations

3

Catalyst‐Free Visible Light‐Driven Hydrosulfonylation of Alkenes and Alkynes with Sulfonyl Chlorides in Water DOI

Xi‐Rui Xia,

Juan Du, Yuxing Zhang

et al.

ChemSusChem, Journal Year: 2024, Volume and Issue: unknown

Published: June 8, 2024

Abstract A convenient and sustainable method for synthesizing sulfonyl‐containing compounds through a catalyst‐free aqueous‐phase hydrosulfonylation of alkenes alkynes with sulfonyl chlorides under visible light irradiation is presented. Unactivated alkenes, electron‐deficient alkyl aryl can be hydrosulfonylated various at room temperature excellent yields geometric selectivities by using tris(trimethylsilyl)silane as hydrogen atom donor silyl radical precursor to activate chlorides. Mechanistic studies revealed that the photolysis in aqueous solution produce crucial success this reaction.

Language: Английский

Citations

3

Reactions of alkynes with C–S bond formation: recent developments DOI

Yuemei Xu,

S. ZHANG, Dayun Huang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(32), P. 6443 - 6484

Published: Jan. 1, 2024

Alkynes are important in organic synthesis. This review mainly focuses on the recent advances (2013–2023) alkynes with C–S bond formation, based more than 30 kinds of sulfur reagents.

Language: Английский

Citations

2