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

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 f...

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Bibliographic Details
Published in:ACS catalysis 2020-02, Vol.10 (3), p.2009-2025
Main Authors: Leitch, Jamie A, Rossolini, Thomas, Rogova, Tatiana, Maitland, J. Andrew P, Dixon, Darren J
Format: Article
Language:English
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Summary: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.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.9b05011