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Visible-Light-Promoted Intramolecular α-Allylation of Aldehydes in the Absence of Sacrificial Hydrogen Acceptors

Jia-Li Liu, Jia-Lin Tu and Feng Liu*

*Department of Medicinal Chemistry, College of Pharmaceutical Sciences, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, People's Republic of China, Email:

J. Li, J.-L. Tu, F. Liu, Org. Lett., 2020, 22, 7369-7372.

DOI: 10.1021/acs.orglett.0c02742 (free Supporting Information)

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The combination of photoredox, cobaloxime, and amine catalysis mediates a radical cyclization of aldehydes with pendant alkenes to provide a variety of 5-, 6-, and 7-membered ring products with alkene transposition in good yields. The reaction exhibits wide functional group compatibility and occurs under mild conditions with extrusion of H2.

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proposed mechanism


Key Words

piperidines, photochemistry

ID: J54-Y2020