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可见光介导的杂芳烃的直接C-H芳基化和烷基化反应

Visible Light-Mediated Direct C-H Aroylation and Alkylation of Heteroarenes.

作者信息

Chang Rui, Fang Jie, Chen Jian-Qiang, Liu Dan, Xu Guo-Qiang, Xu Peng-Fei

机构信息

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.

出版信息

ACS Omega. 2019 Aug 14;4(9):14021-14031. doi: 10.1021/acsomega.9b01674. eCollection 2019 Aug 27.

Abstract

Herein, we describe the photocatalytic generation of nucleophilic aroyl radicals from simple aroyl chlorides as a universal and efficient cross-coupling strategy for the direct aroylation of heteroarenes. Furthermore, visible light-mediated direct alkylation of heteroarenes has also been achieved using unactivated bromoalkanes as radical precursors. These two strategies feature high functional group tolerance, exclusive regioselectivity for reaction at the more electrophilic position of heteroarenes, easily accessible substrates, and mild reaction conditions. Moreover, mechanism studies of two reactions are carried out to support our hypotheses.

摘要

在此,我们描述了从简单的芳酰氯光催化生成亲核芳酰基自由基,作为一种通用且高效的交叉偶联策略,用于杂芳烃的直接芳酰化反应。此外,使用未活化的溴代烷烃作为自由基前体,也实现了可见光介导的杂芳烃直接烷基化反应。这两种策略具有高官能团耐受性、对杂芳烃更亲电位置反应的专一区域选择性、易于获得的底物以及温和的反应条件。此外,还对这两个反应进行了机理研究以支持我们的假设。

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