KOtBu-Mediated Reductive Cyanation of Tertiary Amides for Synthesis of α-Aminonitriles

Liwen Liu, Yu Liu, Xue Shen, Xiao Zhang, Shengqi Deng and Yang Chen*

*Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, Chengdu 610106, China, Email: chenyang1cdu.edu.cn

L . Liu, Y. Liu, X. Shen, X. Zhang, S. Deng, Y. Chen, J. Org. Chem., 2022, 87, 6321-6329.

DOI: 10.1021/acs.joc.1c02835

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Abstract

A simple, mild, catalyst-free, and efficacious KOtBu-mediated reductive cyanation reaction of tertiary amides provides a series of α-aminonitriles in good yields under hydrosilylation conditions with good functional group tolerance. The reaction works well with readily available amide substrates, cheap KOtBu, and a commercially available hydrosilane (EtO)₃SiH and the workup is convenient.

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proposed mechanism

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Key Words

α-Aminonitriles, Triethoxysilane

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ID: J42-Y2022