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

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 e...

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Bibliographic Details
Published in:Chemical reviews 2022-01, Vol.122 (2), p.2353-2428
Main Authors: Kwon, Kitae, Simons, R. Thomas, Nandakumar, Meganathan, Roizen, Jennifer L
Format: Article
Language:English
Subjects:
Catalysis
Chemistry Techniques, Synthetic
Chemists
Light
Nitrogen
Nitrogen - chemistry
Photocatalysis
Photoredox catalysis
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Summary: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.
ISSN:0009-2665
1520-6890
DOI:10.1021/acs.chemrev.1c00444