Regio- and Stereoselective β-Sulfonylamination of Alkynes via Photosensitized Bifunctional N–S Bond Homolysis

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-12-04 DOI:10.1021/acs.orglett.4c04091

Tonglv Pu, Si-Hai Wu, Liuyan Cai, Wenjia Pu, Yilong Yuan, Zhenjing Zhuang, Shumin Yang, Lianhui Wang

引用次数: 0

Abstract

Nitrogen central radicals (NCRs) are versatile synthetic intermediates for creating functional nitrogen-containing molecules. Herein, a photosensitized β-sulfonylamination of terminal alkynes as well as acetylene has been established by employing N-sulfonyl heteroaromatics as bifunctional reagents (BFRs) to efficiently deliver versatile (E)-β-sulfonylvinylamines with excellent regio- and stereoselectivities. Mechanistic studies suggest a base-accelerated energy transfer (EnT) photocatalysis involving aromatic NCR formation, radical addition to alkynes, and sulfonylation processes.

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通过光敏双功能N-S键均解的区域和立体选择性炔的β-磺基层化

氮中心自由基（NCRs）是一种多功能合成中间体，用于生成功能性含氮分子。本文采用n -磺酰基杂芳烃作为双功能试剂（BFRs），建立了末端炔和乙炔的光敏β-磺酰基层化反应，以高效地递送具有优异区域选择性和立体选择性的多功能(E)-β-磺酰基乙烯胺。机理研究表明，碱加速能量转移（EnT）光催化涉及芳香族NCR形成、炔基加成和磺化过程。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.

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