光氧化还原镍催化n -芳基丙烯酰胺与烷基溴的自由基环化。

IF 2.9 3区 化学 Q1 CHEMISTRY, ORGANIC
Yan-Ling Liu , Liu-Shuo Shi , Xian-Chen He , Jie Gao , Ke-Rong Li , Hao-Yue Xiang , Kai Chen , Hua Yang
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引用次数: 0

摘要

3,3-二取代吲哚是一类重要的生物活性分子,通常存在于各种生物活性化合物中。在这项工作中,我们提出了一种光氧化还原镍催化的n -芳基丙烯酰胺和易于获得的烷基溴之间的分子间环化反应,该反应以中高收率提供了各种3,3-二取代氧吲哚。我们的机制研究表明,通过反应性Ni(I)物种的单电子转移还原烷基溴是驱动这种激进级联转变的关键步骤。这种方法有几个优点,包括温和的反应条件、广泛的官能团耐受性和简单的检查程序。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Photoredox nickel-catalyzed radical cyclization of N-arylacrylamides with alkyl bromides†

Photoredox nickel-catalyzed radical cyclization of N-arylacrylamides with alkyl bromides†
3,3-Disubstituted oxindoles constitute a significant class of biologically active molecules, often found in a wide range of bioactive compounds. In this work, we present a photoredox nickel-catalyzed intermolecular cyclization between N-arylacrylamides and readily accessible alkyl bromides, which affords a diverse range of 3,3-disubstituted oxindoles in moderate to high yields. Our mechanistic studies reveal that the reduction of alkyl bromides via single-electron transfer from a reactive Ni(i) species is a critical step in driving this radical cascade transformation. This approach offers several advantages, including mild reaction conditions, broad functional group tolerance, and a simple workup procedure.
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来源期刊
Organic & Biomolecular Chemistry
Organic & Biomolecular Chemistry 化学-有机化学
CiteScore
5.50
自引率
9.40%
发文量
1056
审稿时长
1.3 months
期刊介绍: Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
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