Visible-Light-Induced Dual C(sp³)-H Bond Functionalization of Tertiary Amine via Hydrogen Transfer to Carbene and Subsequent Cycloaddition

Kaixiu Luo, Yongqiang Zhao, Zhiliang Tang, Weina Li, Jun Lin and Yi Jin*

*Key Laboratory of Medicinal Chemistry for Natural Resource, School of Chemical Science and Technology, Yunnan University, Kunming 650091, People’s Republic of China, Email: jinyiynu.edu.cn

K. Luo, Y. Zhao, Z. Tang, W. Li, J. Li, Y. Jin, Org. Lett., 2022, 24, 6335-6340.

DOI: 10.1021/acs.orglett.2c02557

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Abstract

A dual C(sp³)-H bond functionalization of tertiary amines through hydride-transfer-induced dehydrogenation, followed by cycloaddition to substituted N-hydroxyimoyl chlorides in the presence of an easily preparable diazoester under mild, redox-neutral conditions provides functionalized isoxazoldines in good yields.

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proposed mechanism

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Key Words

2-isoxazolines, photochemistry

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ID: J54-Y2022