NBS-Promoted Sulfenylation of Sulfinates with Disulfides Leading to Unsymmetrical or Symmetrical Thiosulfonates

被引：55

作者：

Liang Gaigai ^{[1
]}

Liu Miaochang ^{[1
]}

Chen Jiuxi ^{[1
]}

Ding Jinchang ^{[1
,2
]}

Gao Wenxia ^{[1
]}

Wu Huayue ^{[1
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Zhejiang, Peoples R China

[2] Wenzhou Vocat & Tech Coll, Wenzhou 325035, Zhejiang, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2012年 / 30卷 / 07期

基金：

中国国家自然科学基金;

关键词：

sulfenylation; N-bromosuccinimide (NBS); sulfinate; disulfide; thiosulfonate; ARYLBORONIC ACIDS; CHARCOAL N2O4/CHARCOAL; SELECTIVE OXIDATION; ORGANIC DISULFIDES; CATALYZED ADDITION; CARBONYL-COMPOUNDS; FACILE SYNTHESIS; ESTER SYNTHESIS; S-ESTERS; ALDEHYDES;

D O I：

10.1002/cjoc.201200028

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly practical method to access unsymmetrical and symmetrical thiosulfonates in moderate to excellent yields has been developed through NBS-promoted sulfenylation of sulfinates with disulfides. The present process enables the use of two RS in RSSR and shows broad functional group tolerance, which represents an atom-economical and practical procedure for the synthesis of thiosulfonates. A plausible mechanism for the role of NBS as a promoter for the cleavage of disul?des generating N-(organothio)succinimide that then undergos facile sulenylation with sulfinates is proposed.

引用

页码：1611 / 1616

页数：6

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