4.6 Article

Direct Aldehyde Csp2-H Functionalization through Visible-Light-Mediated Photoredox Catalysis

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 63, Pages 15899-15902

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201704224

Keywords

aldehydes; C-H activation; cross-coupling reactions; photocatalysis; synergistic catalysis

Funding

  1. National Research Foundation [NRF2016NRF-NSFC002-005]
  2. Ministry of Education, Singapore [MOE 2013-T3-1-002]

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The development of methods for carbon-carbon bond formation under benign conditions is an ongoing challenge for synthetic chemists. In recent years there has been considerable interest in using selective C-H activation as a direct route for generating reactive intermediates. Herein, the use of visible-light-mediated dual photoredox organocatalysis as a mild and effective method for C-sp2-H activation of aldehydes is reported, resulting in the generation of acyl radicals. These nucleophilic acyl radical species can undergo either addition to electrophilic alkenes or nickel-catalyzed cross-coupling reactions to provide a quick access to broad range of unsymmetrical ketones, which are abundantly found in many organic building blocks.

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