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α-Amino Radicals via Photocatalytic Single-Electron Reduction of Imine Derivatives

Jamie A. Leitch, Thomas Rossolini, Tatiana Rogova, J. Andrew P. Maitland, Darren J. Dixon

2020ACS Catalysis179 citationsDOI

Abstract

The construction and manipulation of amine-containing architectures is of importance to academic and industrial development and discovery programs. The photochemical single-electron reduction of imine derivatives to generate α-amino radical intermediates has emerged as a powerful umpolung strategy for opening up underexplored routes to such amine motifs. Furthermore, these radicals have been shown to engage in a wide variety of chemistry, including radical–radical coupling, addition to electrophiles, and reductive amination chemistry. The concept has also begun to see application to iminium ion intermediates and the extension to enantiocontrolled C–C bond formation. This Perspective covers recent efforts in this synthetic strategy to simple and complex amine structures alike.

Topics & Concepts

ImineUmpolungChemistryIminiumRadicalElectrophilePhotoredox catalysisCombinatorial chemistryAmine gas treatingReductive aminationOrganocatalysisAminationRadical ionPhotochemistryPhotocatalysisOrganic chemistryCatalysisEnantioselective synthesisNucleophileIonRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques