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Bpin 介导的级联环化/芳构化反应:官能化吲哚嗪的面选择性合成。

Bpin-Mediated Cascade Cyclization/Aromatization Reaction: Facial Access to Functionalized Indolizines.

机构信息

School of Pharmacy, Key Laboratory of Prevention and Treatment of Cardiovascular and Cerebrovascular Diseases of Ministry of Education, Gannan Medical University, Ganzhou 341000, PR China.

School of Pharmacy, Gannan Medical University, Ganzhou 341000, PR China.

出版信息

Org Lett. 2022 Oct 14;24(40):7372-7377. doi: 10.1021/acs.orglett.2c02905. Epub 2022 Sep 29.

Abstract

Herein, a Bpin-mediated radical cascade cyclization/aromatization reaction of enaminone with pyridine is described. This strategy provides a practical way for the construction of valuable functionalized indolizines under metal-, external oxidant-, and base-free conditions, which could be compatible with various kinds of functional groups, such as halogen, π-system, heterocycle, ferrocenyl, etc. A preliminary mechanism investigation indicated that the pyridine-boryl radical formed in situ triggered the reaction to occur.

摘要

本文描述了一种 Bpin 介导的烯胺酮与吡啶的自由基级联环化/芳构化反应。该策略为在无金属、无外部氧化剂和无碱条件下构建有价值的功能化吲哚嗪提供了一种实用的方法,该方法可以与各种官能团兼容,如卤素、π-体系、杂环、二茂铁基等。初步的机理研究表明,原位形成的吡啶硼基自由基引发了反应的发生。

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