镍催化的吲哚与烷基溴的自由基氢烷基化反应

IF 1.7 4区 化学 Q3 CHEMISTRY, ORGANIC Synlett Pub Date : 2024-09-04 DOI:10.1055/a-2382-0292
Hao-Tian Dai, Xu-Lun Huang, Yuan-Zheng Cheng, Shu-Li You
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引用次数: 0

摘要

吲哚衍生物的脱芳烃化为获得吲哚啉框架提供了一种直接的方法。然而,对含有缺电子基团的吲哚进行高效脱芳烃反应的技术仍未得到充分发展。本文报告了一种镍催化的分子间氢烷基脱芳烃反应,通过单电子转移过程将吲哚与简单的溴化烷基进行反应。各种带有不同官能团的吲哚衍生物都能与该方案相容,并能与伯基、仲基或叔基烷基溴化物反应,以良好的收率(高达 82%)和优异的非对映选择性(高达 >20:1)得到一系列吲哚类化合物。值得注意的是,当使用末端烷基溴作为自由基前体时,观察到了镍介导的氢原子转移过程,从而得到了支化产物。
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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Nickel-Catalyzed Radical Hydroalkylative Dearomatization of Indoles with Alkyl Bromides

Dearomatization of indole derivatives offers a straightforward approach to accessing the indoline framework. However, highly efficient dearomatization of indoles bearing electron-deficient groups remains underdeveloped. Herein, a nickel-catalyzed intermolecular hydroalkylative dearomatization reaction of indoles with simple alkyl bromides through a single-electron-transfer process is reported. A wide variety of indole derivatives bearing various functional groups were compatible with this protocol and reacted with primary, secondary, or tertiary alkyl bromides to afford a series of indolines in good yields (up to 82%) and with excellent diastereoselectivity (up to >20:1). Notably, a nickel-mediated hydrogen-atom-transfer process was observed when terminal alkyl bromides were employed as the radical precursors, which resulted in branched products.

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来源期刊
Synlett
Synlett 化学-有机化学
CiteScore
3.40
自引率
5.00%
发文量
369
审稿时长
1 months
期刊介绍: SYNLETT is an international journal reporting research results and current trends in chemical synthesis in short personalized reviews and preliminary communications. It covers all fields of scientific endeavor that involve organic synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines and offers the possibility to publish scientific primary data.
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