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一锅法串联氧化溴化和磺酰胺的氨化反应合成亚磺酰胺。

One-Pot Tandem Oxidative Bromination and Amination of Sulfenamide for the Synthesis of Sulfinamidines.

机构信息

Natural Products Research Center, Chengdu Institution of Biology, Chinese Academy of Science, Chengdu 610041, Sichuan, China.

出版信息

J Org Chem. 2023 Apr 7;88(7):4581-4591. doi: 10.1021/acs.joc.3c00042. Epub 2023 Mar 16.

Abstract

The sulfinamidines as aza analogues of sulfinamides received limited attention from both organic chemists and pharmaceutical chemists. Herein, we present a tandem oxidative/nucleophilic substitution approach for the synthesis of sulfinamidines in high yield (up to 98%). This cascade reaction method is enabled by N-bromosuccinimide (NBS) as an oxidant and diverse readily available amines as nucleophiles without any additives or catalysts. Notably, this method is highly time-economical, safe to operate, and easy to scale up and has excellent functional group compatibility.

摘要

亚磺酰胺的氮类似物——磺胺亚胺,受到有机化学家和药物化学家的关注有限。在此,我们提出了一种串联氧化/亲核取代方法,可高产率(高达 98%)合成磺胺亚胺。该级联反应方法以 N-溴代丁二酰亚胺(NBS)作为氧化剂,各种易得的胺作为亲核试剂,无需任何添加剂或催化剂。值得注意的是,该方法具有高度的时间经济性、操作安全性、易于放大和对功能基团具有良好的兼容性。

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