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Photoredox Radical/Polar Crossover Enables Construction of Saturated Nitrogen Heterocycles

Loc R. E. Pantaine, John A. Milligan, Jennifer K. Matsui, Christopher B. Kelly*, Gary A. Molander*

*Virginia Commonwealth University, Richmond, Virginia 23284-9069; University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States, Email: cbkellyvcu.edu, gmolandrsas.upenn.edu

L. R. E. Pantaine, J. A. Milligan, J. K. Matsui, C. B. Kelly, G. A. Molander, Org. Lett., 2019, 21, 2317-2321.

DOI: 10.1021/acs.orglett.9b00602 (free Supporting Information)



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Abstract

With the aid of visible light irradiation, the reaction of photocatalytically generated alkyl radicals possessing pendant leaving groups with imines provides substituted pyrrolidines, piperidines, and azepanes under mild, redox-neutral conditions.

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Key Words

pyrrolidines, photochemistry


ID: J54-Y2019