Electrophotocatalytic Thiocyanation and Sulfonylation Cyclization of Unactivated Alkenes DOI
Yingchun Ma,

Ping Yu,

Ruoyu Qin

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 18, 2024

We report an electrophotocatalytic process that enables the thiocyanation and sulfonylation/cyclization of alkenes. It is applicable to a wide range unactivated alkenes, using inexpensive photocatalyst 2,4,6-triphenylpyrylium tetrafluoroborate (TPPT) produce diverse array heterocycles containing sulfonyl thiocyano groups with good functional group tolerance. The protocol operates under mild, chemical oxidant- transition-metal-free, broad scope substrates. Preliminary mechanistic studies suggest reaction involves combination electrolysis reductive quenching photocatalytic cycle TPPT.

Language: Английский

Electrochemical Sulfonylation/Cyclization of N-Alkenylacrylamides with Sodium Sulfinates or Sulfonyl Hydrazides DOI
Zhixian Yang,

Lu-Cai Ding,

Gui-Hong Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10660 - 10677

Published: July 18, 2024

Two general protocols for the regioselective electrochemically enabled sulfonylation cyclization of

Language: Английский

Citations

8
Catalyst-Free Radical Dearomatization of Phenols with Aryldiazonium Tetrafluoroborates and DABCO·(SO2)2 DOI
Xingxian Zhang, Guanyinsheng Qiu, Shaoyu Li

et al.

Synlett, Journal Year: 2025, Volume and Issue: unknown

Published: March 4, 2025

Abstract A catalyst-free, three-component dearomatization of phenols with aryldiazonium tetrafluoroborates and DABCO·(SO2)2 has been developed for the synthesis 4-(arylsulfonyl)cyclohex-2,5-dien-1-one scaffolds. This method offers mild reaction conditions high step efficiency, providing a green efficient strategy phenols. Mechanistic studies indicated that this transformation relies on tandem radical sulfur dioxide insertion process.

Language: Английский

Citations

0
Photoredox Radical Cyclization of o-Vinylaryl Isocyanides and Aryldiazonium Tetrafluoroborates for the Synthesis of 2,4-Disubstituted Quinolines DOI
Min Gao, Chuan Ding, Peng‐Fei Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 23, 2025

Quinolines, a significant part of nitrogen-containing heterocycles, are widely found in functional compounds. Herin, photochemical radical cyclization reaction o-vinylaryl isocyanides and aryldiazonium tetrafluoroborates, has been reported to build 2,4-diaryl quinolines. Readily accessible aryl diazonium salts were utilized as precursors at room temperature. This approach allowed good group tolerance substrate applicability.

Language: Английский

Citations

0
Alkyl Radical Initiated Cyclization/Cascade for Synthesizing Lactam‐Substituted Alkyl Sulfones DOI
Li‐Jun Wu,

Kai‐Yi Zhang,

Pei Yang

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(16), P. 1853 - 1859

Published: April 17, 2024

Comprehensive Summary An alkyl radical initiated cyclization/tandem reaction of bromides and electrophiles by using potassium metabisulphite (K 2 S O 5 ) as a connector is developed for the synthesis various lactam‐substituted sulfones. Notably, this process does not require metal catalyst or powder reductant, highlighting its environmentally friendly features. The demonstrates outstanding substrate adaptability high tolerance towards diverse functional groups. Furthermore, biologically active molecules commercially available drugs with late‐stage modification are also highly compatible transformation. Mechanistic studies revealed that proceeds through single‐step involving intramolecular cyclization, "SO " insertion, external incorporation.

Language: Английский

Citations

2
A photoinduced three‐component reaction of thianthrenium salts, DABCO·(SO2)2, and benzyl ether substituted alkenes DOI
Ji Zhang, J N Cen, Shengqing Ye

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(14), P. 3130 - 3137

Published: May 31, 2024

Abstract A photoinduced three‐component reaction of thianthrenium salts, DABCO ⋅ (SO 2 ) , and benzyl ether substituted alkenes is developed, affording δ‐hydroxylsulfones with good functional group tolerance. This transformation proceeds through an anti‐Markovnikov hydrosulfonylation under a mild condition. Mechanism studies indicates that this undergoes radical pathway involving sulfur dioxide insertion 1,5‐hydrogen transfer processes.

Language: Английский

Citations

2
DABCO‐Mediated Photoelectrochemical Three‐Component Sulfonocyclization of 3‐Aza‐1,5‐dienes DOI

Lu-Cai Ding,

Gui-Hong Yang,

Li Luo

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 2, 2024

Comprehensive Summary Herein, we report a rare example of three‐component net‐oxidative sulfonylation SO 2 surrogate with an oxidatively activated radical precursor under mild and metal‐ external‐oxidant‐free conditions. The mildness sustainability the reaction are enabled by photoelectrocatalysis, 3‐aza‐1,5‐dienes, organotrifluoroborates 1,4‐diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) undergo sulfonylative cyclization to afford sulfono 4‐pyrrolin‐2‐ones in atom‐economical manner broad substrate scope good functional‐group tolerance. protocol is amenable late‐stage diversification complex molecular architectures as well gram‐scale synthesis. Sunlight could be used light source, conducted all‐solar mode using commercially available photovoltaic panel generate electricity situ . Mechanistic studies reveal that generated (DABCO), which was generally innocent previous reactions, functions electron shuttle between photocatalytic cycle reactants.

Language: Английский

Citations

2
Catalyst-Free Radical Carbosulfonylation of Enamides with Indoles, Aryldiazonium Tetrafluoroborates, and DABCO·(SO2)2 DOI
Changmei Zhang, Hao Cheng, Yuanyuan An

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 23, 2024

Herein, we have developed a catalyst-free four-component carbosulfonylation of enamides involving indoles, DABCO·(SO

Language: Английский

Citations

1
Electrophotocatalytic Thiocyanation and Sulfonylation Cyclization of Unactivated Alkenes DOI
Yingchun Ma,

Ping Yu,

Ruoyu Qin

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 18, 2024

We report an electrophotocatalytic process that enables the thiocyanation and sulfonylation/cyclization of alkenes. It is applicable to a wide range unactivated alkenes, using inexpensive photocatalyst 2,4,6-triphenylpyrylium tetrafluoroborate (TPPT) produce diverse array heterocycles containing sulfonyl thiocyano groups with good functional group tolerance. The protocol operates under mild, chemical oxidant- transition-metal-free, broad scope substrates. Preliminary mechanistic studies suggest reaction involves combination electrolysis reductive quenching photocatalytic cycle TPPT.

Language: Английский

Citations

1