Catalyst-Free Regio- and Stereoselective C(sp2)–H Chlorination of Enamides at Room Temperature

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-29 DOI:10.1021/acs.orglett.5c01110

Meng-Liang Deng, Meng-Wei Sheng, Xu-Kang Wen, Ruo-Nan Cao, Meng Li, Teck-Peng Loh, Ming-Zhu Lu

引用次数: 0

Abstract

We disclose herein a catalyst-free, room-temperature protocol for the highly regio- and stereoselective alkenyl C(sp²)–H chlorination of diverse enamides with commercially available, inexpensive N-chlorosuccinimide (NCS) as the electrophilic chlorinating reagent under exceedingly mild conditions. This operationally simple approach features a remarkably broad substrate scope and accommodates excellent functional group tolerance, affording a diverse range of synthetically valuable geometrically defined β-chlorinated enamides in high yields with an exclusive E configuration.

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室温下无催化剂区域和立体选择性C(sp2) - h氯化反应

我们在此公开了一种无催化剂的室温方案，在非常温和的条件下，用市售的、廉价的n -氯丁二酰亚胺（NCS）作为亲电氯化试剂，对各种酰胺进行高度区域和立体选择性的烯基C(sp2) - h氯化反应。这种操作简单的方法具有非常广泛的底物范围和良好的官能团耐受性，以高收率提供各种具有几何意义的合成价值的β-氯化胺，具有独特的E构型。

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.