Nucleophilic Substitution of Tertiary Sulfonamides: Construction of Sulfonate Esters.

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-03-07 Epub Date: 2025-02-27 DOI:10.1021/acs.orglett.5c00587

Xiangshuai Du, Guodan Lu, Tao Zhang, Congzhou Wang, Yong Wang, Xiaobing Wan

引用次数: 0

Abstract

Under the combined action of trichloroisocyanuric acid (TCCA) and triflic acid (TfOH), tertiary sulfonamides are efficiently activated, leading to the in situ generation of electrophilic sulfonamide salts. These electrophilic salts subsequently undergo nucleophilic substitution by alcohols, resulting in the formation of sulfonate esters under mild conditions. Other advantages of this method include the absence of transition-metal catalysts, broad substrate applicability, and high functional-group tolerance.

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

叔磺酰胺的亲核取代：磺酸酯的构造。

在三氯异氰尿酸（TCCA）和三羧酸（TfOH）的共同作用下，叔胺类化合物被有效活化，导致亲电性磺胺盐的原位生成。这些亲电盐随后被醇亲核取代，在温和条件下形成磺酸酯。该方法的其他优点包括不需要过渡金属催化剂、广泛的底物适用性和高官能团耐受性。

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分钟内获得全文去求助

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.