4.8 Review

Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis

Journal

CHEMICAL REVIEWS
Volume 122, Issue 2, Pages 2353-2428

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.chemrev.1c00444

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Funding

  1. National Institutes of Health [R35GM128741-01]

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This review is a guide for chemists engaged in target-oriented synthesis, summarizing the recent methods and applications of generating nitrogen-centered radicals through photocatalysis. The mild conditions of this approach enable its wide applications in synthesizing various small molecules, highlighting its tremendous utility.
For more than 70 years, nitrogen-centered radicals have been recognized as potent synthetic intermediates. This review is a survey designed for use by chemists engaged in target-oriented synthesis. This review summarizes the recent paradigm shift in access to and application of N-centered radicals enabled by visible-light photocatalysis. This shift broadens and streamlines approaches to many small molecules because visible-light photocatalysis conditions are mild. Explicit attention is paid to innovative advances in N-X bonds as radical precursors, where X = Cl, N, S, O, and H. For clarity, key mechanistic data is noted, where available. Synthetic applications and limitations are summarized to illuminate the tremendous utility of photocatalytically generated nitrogen-centered radicals.

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