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可见光光氧化还原催化的α-酮酸直接脱羧官能团化反应

Visible-Light Photoredox-Catalyzed Direct Decarboxylative Functionalization of α-Keto Acids.

作者信息

Sun Huangbin, Zhang Qianfan, Tang Jie, Chen Xiaowen, Jiang Guofang

机构信息

State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China.

School of Materials and Environmental Engineering, Shenzhen Polytechnic University, Shenzhen 518055, P. R. China.

出版信息

J Org Chem. 2024 Oct 18;89(20):15225-15233. doi: 10.1021/acs.joc.4c02011. Epub 2024 Oct 8.

Abstract

A novel and environmentally friendly photocatalytic strategy is presented for generating acyl radicals from benzoylformic acids, which are subsequently trapped by various sulfone-based SOMOphiles. This strategy provides a robust toolkit to access a variety of synthetically important functionalized aryl-ketone derivatives, which efficiently and directly construct acyl-S, acyl-Se, acyl-C, and acyl-N bonds. The broad substrate scope, excellent functional group compatibility, and mild reaction conditions make this protocol practical and attractive.

摘要

本文提出了一种新颖且环境友好的光催化策略,用于从苯甲酰甲酸生成酰基自由基,随后这些自由基被各种基于砜的亲SOMO试剂捕获。该策略提供了一个强大的工具包,可用于获得各种具有重要合成意义的官能化芳基酮衍生物,能高效且直接地构建酰基 - 硫、酰基 - 硒、酰基 - 碳和酰基 - 氮键。广泛的底物范围、出色的官能团兼容性以及温和的反应条件使该方法实用且具有吸引力。

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