Synthesis 2024; 56(09): 1415-1421
DOI: 10.1055/a-2248-5438
paper

Iodine-Promoted Disproportionate Coupling Reaction of Arylsulfonyl Hydrazides: A Simple and Green Access to Thiosulfonates

Qi Chen
a   School of Chemistry, South China Normal University, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006, P. R. China
,
Zhao-Hua Chen
a   School of Chemistry, South China Normal University, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006, P. R. China
,
Yong-Tong Liang
a   School of Chemistry, South China Normal University, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006, P. R. China
,
Yong Zeng
a   School of Chemistry, South China Normal University, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006, P. R. China
,
Shi-Wei Yu
a   School of Chemistry, South China Normal University, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006, P. R. China
,
Kai Yang
b   College of Pharmacy, Gannan Medical University, Ganzhou 341000, P. R. China
,
Zhao-Yang Wang
a   School of Chemistry, South China Normal University, GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006, P. R. China
› Author Affiliations
This research was supported by Guangdong Basic and Applied Basic Research Foundation (No. 2021A1515012342), National Natural Science Foundation of China (20772035) and Natural Science Foundation of Jiangxi Province (No. 20224BAB203010).


Abstract

An environmentally friendly iodine-promoted disproportionate coupling reaction of arylsulfonyl hydrazides is reported. This strategy can synthesize thiosulfonates with medium to excellent yields, and features a green system, wide applicability of substrates, and easy availability of raw materials. The preliminary mechanistic study reveals that iodine plays an important role in the radical reaction process.

Supporting Information



Publication History

Received: 12 December 2023

Accepted after revision: 17 January 2024

Accepted Manuscript online:
17 January 2024

Article published online:
12 February 2024

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