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用于不对称多硫化物的双二硫试剂的设计。

Design of a Bilateral Disulfurating Reagent for Unsymmetrical Polysulfidation.

机构信息

Key Laboratory of Agri-Food Safety of Anhui Province, School of Resources and Environment,Anhui Agricultural University, Hefei, Anhui, 230036, China.

出版信息

Angew Chem Int Ed Engl. 2023 Jun 19;62(25):e202302861. doi: 10.1002/anie.202302861. Epub 2023 May 9.

Abstract

In this study, we designed a bilateral disulfurating reagent via S-S motif "snip and stitch" processes, allowing diverse functional groups to be bridged via S-S bonds. The reagent is readily synthesized in high yield using a one-step reaction from easily available starting materials and is air-stable. With this reagent, diverse electrophiles including inactivated alkyl Cl/Br/I/OMs and benzyl chloride were sequentially installed on either side of the S-S motif. Natural products, agrochemicals, and pharmaceuticals can be successively cross-linked with S-S bonds. Notably, the disulfurating reagent can be used in cyclic disulfide synthesis. At last, some desired products of this work showed good antibacterial activities, which could be employed as novel candidates to control plant pathogenic bacteria.

摘要

在这项研究中,我们设计了一种通过 S-S 基“剪接”过程的双硫试剂,允许通过 S-S 键桥连各种不同的功能基团。该试剂可以通过一步反应从易得的起始原料以高产率制备,并且具有空气稳定性。使用这种试剂,可以将各种亲电试剂(包括失活的烷基 Cl/Br/I/OMs 和苄基氯)依次安装在 S-S 基的两侧。天然产物、农用化学品和药物可以通过 S-S 键成功交联。值得注意的是,该双硫试剂可用于环状二硫键合成。最后,这项工作的一些期望产物表现出良好的抗菌活性,可作为控制植物病原菌的新型候选物。

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