LiBr-Promoted Reaction of β-Ketodithioesters and Thioamides with Sulfoxonium Ylides to Synthesize Functionalized Thiophenes.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-10-22 DOI:10.1021/acs.orglett.4c03680

Subhasish Ray, Nimisha Gupta, Maya Shankar Singh

引用次数: 0

Abstract

An operationally simple and highly efficient synthesis of functionalized thiophenes has been developed by LiBr promoted heteroannulation of β-ketodithioesters and thioamides with bench-stable sulfoxonium ylides in open air for the first time. This one-pot strategy involves formal Csp³-H bond insertion/intramolecular cyclization cascade, featuring readily accessible starting materials, TM and additive-free condition, broad substrate scope, high functional group compatibility, and scalability. Moreover, the carbonyl, thiomethyl, and amino groups in the resulting thiophene provide a good handle on downstream transformations.

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LiBr 促进β-酮二硫酯和硫酰胺与亚磺酰氧铵的反应，合成功能化噻吩。

通过 LiBr 促进的β-酮二硫酯和硫酰胺与台式稳定的锍酰化物在露天下的异annulation，首次开发出了一种操作简单、高效的官能化噻吩合成方法。这种一锅策略涉及正式的 Csp3-H 键插入/分子内环化级联，具有容易获得的起始材料、无 TM 和添加剂条件、广泛的底物范围、高官能团兼容性和可扩展性等特点。此外，所得噻吩中的羰基、硫甲基和氨基也为下游转化提供了良好的条件。

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.