4.6 Article

Visible-Light-Promoted Metal-Free Aerobic Oxidation of Primary Amines to Acids and Lactones

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 49, Pages 17566-17570

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201604440

Keywords

acids; aerobic oxidation; amines; carbon-carbon bond cleavage; visible light

Funding

  1. National 973 Program [2015CB856600]
  2. NSFC [21472162, 21573161]

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A unique metal-free aerobic oxidation of primary amines via visible light photocatalytic double carbon-carbon bonds cleavage and multi carbon-hydrogen bonds oxidation was observed. Aerobic oxidation of primary amines could be controlled to afford acids by using dioxane with 18W CFL, and lactones by using DMF with 8W green LEDs, respectively. A plausible mechanism was proposed based on control experiments. This observation showed direct evidences for the fragmentation in the aerobic oxidation of aliphatic primary amines.

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