Selective Synthesis of Unsymmetrical Disulfides from Thiols via Water-Removable SuFEx Reagent.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-29 DOI:10.1021/acs.orglett.5c02260

Jiaman Hou,Minlong Wang,Xinshu Qin,Ruoqing Peng,Hengzhao Li,Xiaohe Zhang,Xiaoxu Zhang,Minhui Han,Jie An

引用次数: 0

Abstract

A SuFEx reagent was designed for chemoselective synthesis of unsymmetrical disulfide, featuring a triethoxysilane moiety and a sulfonyl fluoride group activated by a γ-sulfur atom. It reacts with a more acidic thiol to form a thiosulfonate intermediate, which then couples with a less acidic thiol. The reagent and residual base are easily removed by aqueous workup. This method enables synthesis of both unsymmetrical and symmetrical disulfides. Various unsymmetrical disulfides were synthesized in up to 98% yields using equimolar thiol starting materials, which surpasses SO2F2/Et3N-mediated protocol in efficiency and selectivity.

查看原文本刊更多论文

用可水洗SuFEx试剂从硫醇中选择性合成不对称二硫化物。

设计了一种SuFEx试剂，用于化学选择性合成具有三乙氧基硅烷和γ-硫原子活化的磺酰氟基团的不对称二硫化物。它与酸性较强的硫醇反应形成硫代磺酸盐中间体，然后与酸性较弱的硫醇偶联。试剂和残余碱很容易通过水处理去除。这种方法可以合成不对称和对称的二硫化物。以等摩尔硫醇为原料合成各种不对称二硫化物，收率高达98%，在效率和选择性上均优于SO2F2/ et3n介导的方案。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.