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Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications

Lixing Zhao, Chenyang Hu, Xuefeng Cong, Gongda Deng, Liu Leo Liu, Meiming Luo and Xiaoming Zeng*

*Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China, Email: zengxiaomingscu.edu.cn

L. Zhao, C. Hu, X. Cong, G. Deng, L. L. Liu, M. Luo, X. Zeng, J. Am. Chem. Soc., 2021, 143, 1618-1629.

DOI: 10.1021/jacs.0c12318


Abstract

A complex of a cyclic (alkyl)(amino)carbene (CAAC) ligand with chromium catalyzes a mild, chemoselective, and efficient deoxygenative hydroboration of nitro compounds to provide a broad range of anilines, as well as heteroaryl and aliphatic amine derivatives. The CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin and serves as an H-shuttle.

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Key Words

reduction of nitro compounds, pinacolborane


ID: J48-Y2021