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Anti-Markovnikov Hydroamination of Alkenes Catalyzed by an Organic Photoredox System

Tien M. Nguyen and David A. Nicewicz*

*Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States, Email: nicewiczunc.edu

T. M. Nguyen, D. A. Nicewicz, J. Am. Chem. Soc., 2013, 135, 9588-9591.

DOI: 10.1021/ja4031616 (free Supporting Information)


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Abstract

A metal-free method for a direct anti-Markovnikov hydroamination of unsaturated amines is enabled by irradiation of the amine substrates with visible light in the presence of catalytic quantities of easily synthesized 9-mesityl-10-methylacridinium tetrafluoroborate and thiophenol as a hydrogen-atom donor. The reaction furnished nitrogen-containing heterocycles with complete regiocontrol.


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Key Words

pyrrolidines


ID: J48-Y2013