4.8 Article

Photoredox-Catalyzed Reductive Coupling of Aldehydes, Ketones, and Imines with Visible Light

期刊

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 30, 页码 8828-8832

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WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201501556

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diamines; photosensitizers; pinacol coupling; proton-coupled electron transfer; radical anions

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Ketyl radical and amino radical anions, valuable reactive intermediates for CC bond-forming reactions, are accessible through a CO/CNR umpolung. However, their utilization in catalysis remains largely underdeveloped owing to the high reduction potential of carbonyl compounds and imines. In the context of photoredox catalysis, tertiary amines are commonly employed as sacrificial co-reducing agents. Herein, an additional role of the amine is proposed, in which it is essential for the organocatalytic substrate activation. The combination of photoredox catalysis and carbonyl/imine activation enables the reductive coupling of aldehydes, ketones, and imines under mild reaction conditions.

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