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α-氨基自由基促进的烯烃与多卤代烷烃和杂芳烃的双官能化反应。

α-Amino Radical-Mediated Difunctionalization of Alkenes with Polyhaloalkanes and -Heteroarenes.

机构信息

College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou 311121, P. R. China.

Key Laboratory of Pollution Exposure and Health Intervention of Zhejiang Province, College of Biology and Environmental Engineering, Zhejiang Shuren University, Hangzhou 310015, P. R. China.

出版信息

Org Lett. 2023 Mar 24;25(11):1994-1998. doi: 10.1021/acs.orglett.3c00647. Epub 2023 Mar 15.

Abstract

Herein, we report a mild and practical protocol for the α-perchloroalkyl β-heteroarylation of alkenes using available chloroform as the dichloromethyl source via α-amino radical-mediated halogen-atom transfer. Various substrates are compatible under mild reaction conditions, providing the corresponding products in moderate to good yields. This strategy gives an efficient and convenient method for the introduction of chloroalkyl motifs into -heteroarenes. The control experiment demonstrates that the α-amino radical generated is a key intermediate in the transformation.

摘要

本文报道了一种温和实用的方法,通过α-氨基自由基介导的卤原子转移,利用易得的氯仿作为二氯甲基源,实现了烯烃的α-高氯代烷基-β-杂芳基化反应。在温和的反应条件下,各种底物都具有兼容性,以中等至良好的收率得到相应的产物。该策略为在 -杂芳环中引入氯代烷基提供了一种高效、便捷的方法。控制实验表明,生成的α-氨基自由基是转化中的关键中间体。

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