Electrochemical Desaturation and β-Thiocyanation of Cyclic Amides

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-12-19 DOI:10.1021/acs.orglett.4c04141
Kaili Miao, Jin Zhang, Jiaxin Chen, Lin-Bao Zhang, Ming Li, Lirong Wen, Weisi Guo
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Abstract

The site-selective functionalization of cyclic amides provides an attractive protocol for the synthesis of valuable molecules. We report herein an electrochemical desaturation and β-thiocyanation of cyclic amides under external oxidant-free conditions. This method exhibits broad functional group tolerance, excellent selectivity, mild reaction conditions and can be applied for late-stage functionalization of bioactive molecules. Mechanistic studies indicate that an enamide intermediate might be involved.

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环酰胺的电化学脱饱和和β-硫氰化
环酰胺的位点选择性功能化为有价值分子的合成提供了一个有吸引力的方案。本文报道了环酰胺在无氧化条件下的电化学脱饱和和β-硫氰化反应。该方法具有官能团耐受性广、选择性好、反应条件温和等特点,可用于生物活性分子的后期功能化。机理研究表明,可能涉及一种酰胺中间体。
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来源期刊
Organic Letters
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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