Loïc R E Pantaine1, John A Milligan1, Jennifer K Matsui1, Christopher B Kelly2,3, Gary A Molander1. 1. Roy and Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , 231 South 34th Street , Philadelphia , Pennsylvania 19104-6323 , United States. 2. Department of Chemistry , Virginia Commonwealth University , 1001 West Main Street , P.O. Box 842006, Richmond , Virginia 23284-9069 , United States. 3. Medicines for All Institute , Virginia Commonwealth University , Biotech 8 737 North Fifth Street , Richmond , Virginia 23219-1441 , United States.
Abstract
Photoredox-mediated radical/polar crossover (RPC) processes offer new avenues for the synthesis of cyclic molecules. This process has been realized for the construction of medium-sized saturated nitrogen heterocycles. Photocatalytically generated alkyl radicals possessing pendant leaving groups engage imines in C-C bond formation, and subsequent reduction of the intermediate nitrogen-centered radical triggers anionic ring closure. With the aid of visible light irradiation, substituted pyrrolidines, piperidines, and azepanes can be prepared under mild, redox-neutral conditions.
Photoredox-mediated radical/polar crossover (RPC) processes offer new avenues for the synthesis of cyclic molecules. This process has been realized for the construction of medium-sized saturated nitrogen heterocycles. Photocatalytically generated n class="Chemical">alkyl radicals possessing pendant leaving groups engage imines in C-C bond formation, and subsequent reduction of the intermediate nitrogen-centered radical triggers anionic ring closure. With the aid of visible light irradiation, substituted pyrrolidines, piperidines, and azepanes can be prepared under mild, redox-neutral conditions.
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