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Allylic Amination of Highly Substituted Alkenes Enabled by Photoredox Catalysis and Cu(II)-Mediated Radical–Polar Crossover

Grace A. Lutovsky, Ellie F. Plachinski, Nicholas L. Reed, Tehshik P. Yoon

2023Organic Letters12 citationsDOIOpen Access PDF

Abstract

Allylic amination reactions enable the conversion of alkene feedstocks into value-added products with significant synthetic versatility. Here we describe a method for allylic amination involving photoredox activation and Cu(II)-mediated radical-polar crossover. A range of structurally varied allylic amines can be accessed using this strategy. The regioselectivity of this process is complementary to those of conventional methods for allylic amination.

Topics & Concepts

Allylic rearrangementAminationChemistryRegioselectivityAlkeneCatalysisCombinatorial chemistryOrganic chemistryPhotochemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsRadical Photochemical Reactions