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Photoinduced Radical Alkylation of Cyclic Aldimines with Unactivated C(sp3)-H Alcohols Enabled by Alcohol-Directed
Jie Liu1, Guozheng Ma1, Yi Liang1
1Department of College of Chemistry & Materials, Gannan Normal University, Ganzhou, Jiangxi 341000, China.
Abstract:
Herein, we report a mild and photoinduced radical alkylation of cyclic aldimines enabled by visible light. By leveraging visible-light-induced phenyliodine bis(trifluoroacetate) (PIFA) activation of free alcohols, this approach generates alkoxyl radicals via intramolecular 1,5-hydrogen atom transfer (1,5-HAT)─a practical and versatile method for remote C(sp3)-H functionalization known for its excellent regioselectivity. These alkoxyl radicals serve as alkylation agents, enabling efficient remote C(sp3)-H bond functionalization between cyclic aldimines and alcohols. The method features accessible starting materials, high atom economy, simple operation, and mild conditions, providing a practical and versatile pathway for the modification of cyclic aldimine derivatives.
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