Merging Gold/Copper Catalysis and Copper/Photoredox Catalysis: An Approach to Alkyl Oxazoles from N-Propargylamides

Yantao Liu, Keyong Zhu, Yuting Kong, Xiao Li, Jie Cui, Yifan Xia, Jingjing Zhao*, Shaofeng Duan and Pan Li*

*College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, P. R. China, Email: zhaojingjinghenu.edu.cn, panlihenu.edu.cn

Y. Liu, K. Zhu, Y. Kong, X. Li, K. Cui, Y. Xia, J. Zhao, S. Duan, P. Li, J. Org. Chem., 2021, 86, 18247-18256.

DOI: 10.1021/acs.joc.1c02668

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Abstract

The combination of gold/copper catalysis and copper/photoredox catalysis enables a mild and highly efficient approach to alkyl oxazoles from N-propargylamides and alkyl halides in very good yields with wide functional-group compatibility under blue-light irradiation. The copper catalyst accelerates protodeauration of vinyl gold intermediates and improves photoredox catalysis.

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proposed mechanism

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Key Words

oxazoles, photochemistry

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ID: J42-Y2021