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Copper-Catalyzed Asymmetric Cyanation of Propargylic Radicals via Direct Decarboxylation of Propargylic Carboxylic Acids

Guang'an Zhang, Yonghong Pei, Junwei Wang, Xinyu Zhu, Zhongxian Li*, Fengqian Zhao* and Junliang Wu*

*Henan Academy of Sciences, Zhengzhou, Henan 450002; Zhengzhou University, Zhengzhou, Henan 450001, P. R. China, Email: lzxnew337126.com, fqzhaozzu.edu.cn, wujlzzu.edu.cn

G. Zhang, Y. Pei, J. Wang, X. Zhu, Z. Li, F. Zhao, F. Zhao, J. Wu, Org. Lett., 2023, 25, 5006-5010.

DOI: 10.1021/acs.orglett.3c01637


Abstract

A highly atom-economical strategy for a copper-catalyzed synthesis of chiral propargylic cyanides is based on a direct decarboxylation of propargylic carboxylic acids without preactivation. The reactions show excellent selectivity and functional group compatibility. Gram-scale reaction and several conversion reactions from chiral propargylic cyanide have demonstrated the synthetic value of this strategy.

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proposed mechanism



Key Words

cyanation, nitriles, PIDA


ID: J54-Y2023