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Published on: May 21, 2019
Photoredox-Catalyzed Reductive Coupling of Aldehydes, Ketones, and Imines with Visible Light
Masaki Nakajima1, Eleonora Fava1, Sebastian Loescher1
1Institute of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52068 Aachen (Germany).
Abstract:
Ketyl radical and amino radical anions, valuable reactive intermediates for C-C bond-forming reactions, are accessible through a C=O/C=NR 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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