Disproportionate Coupling Reaction of Sodium Sulfinates Mediated by BF3•OEt2: An Approach to Symmetrical/Unsymmetrical Thiosulfonates

被引：90

作者：

Cao, Liang ^{[1
]}

Luo, Shi-He ^{[1
,3
]}

Jiang, Kai ^{[1
]}

Hao, Zhi-Feng ^{[2
]}

Wang, Bo-Wen ^{[1
]}

Pang, Chu-Ming ^{[1
]}

Wang, Zhao-Yang ^{[1
,3
]}

机构：

[1] South China Normal Univ, Sch Chem & Environm, Key Lab Theoret Chem Environm, Minist Educ, Guangzhou 510006, Guangdong, Peoples R China

[2] Guangdong Univ Technol, Sch Chem Engn & Light Ind, Guangzhou 510006, Guangdong, Peoples R China

[3] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, 381 Wushan Rd, Guangzhou 510640, Guangdong, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 16期

关键词：

SULFONYL HYDRAZIDES; DIMETHYL-SULFOXIDE; DUAL CATALYSIS; BOND FORMATION; C-S; ACCESS; ARYL; REARRANGEMENT; ARYLATION; RADICALS;

D O I：

10.1021/acs.orglett.8b01808

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The BF3 center dot OEt2-mediated disproportionate coupling reaction of sodium sulfinates was found for the first time. In this reaction, various S-S(O)(2) bonds can be formed, efficiently giving thiosulfonates in moderate to excellent yields. As a convenient protocol for the synthesis of symmetrical and unsymmetrical thiosulfonates, its reaction mechanism involves the formation of a thiyl radical and sulfonyl radical via a sulfinyl radical disproportionation. What is more, this transformation can also be applied practically as a gram-scale reaction and to the two-step synthesis of sulfone and sulfonamide in one pot in situ using thiosulfonate as an intermediate.

引用

页码：4754 / 4758

页数：5

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