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

Masaki Nakajima, Eleonora Fava, Sebastian Loescher, Zhen Jiang, Magnus Rueping

Research output: Contribution to journalArticlepeer-review

161 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)8828-8832
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number30
DOIs
StatePublished - Jul 20 2015

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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