Nucleophilic Substitution of Tertiary Sulfonamides: Construction of Sulfonate Esters.

IF 4.9 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.

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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.