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Visible-Light Promoted Selective Imination of Unactivated C-H Bonds via Copper-nitrene Intermediates for the Synthesis of 2H-Azirines

Liyan Feng, Chao Yang and Wujiong Xia*

*State Key Laboratory of Urban Water Resource and Environment, Harbin Institute of Technology (Shenzhen), Shenzhen 518055, China, Email:

L. Feng, C. Yang, W. Xia, Org. Lett., 2019, 21, 8323-8327.

DOI: 10.1021/acs.orglett.9b03103

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The combination of a copper and a photoredox catalyst enables the selective imination of unactivated C-H bonds under mild conditions. Trapping of iminyl radicals with copper ions results in high-valent Cu(III) imine intermediates, that quickly form nitrenes and then furnish 2H-azirines. A ring-expansion rearrangement from cyclobutyl oxime derivatives gives α-acylamino cyclopentanones.

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proposed mechanism

Key Words


ID: J54-Y2019