4.8 Article

Chemoselective Organocatalytic Aerobic Oxidation of Primary Amines to Secondary Imines

Journal

ORGANIC LETTERS
Volume 14, Issue 11, Pages 2850-2853

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol301095j

Keywords

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Funding

  1. U.S. Department of Energy [DE-FG02-05ER15690]
  2. NSF [CHE-9208463, CHE-0342998, CHE-9629688, CHE-9974839]
  3. U.S. Department of Energy (DOE) [DE-FG02-05ER15690] Funding Source: U.S. Department of Energy (DOE)

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Biomimetic aerobic oxidation of primary benzylic amines has been achieved by using a quinone catalyst. Excellent selectivity is observed for primary, unbranched benzylic amines relative to secondary/tertiary amines, branched benzylic amines, and aliphatic amines. The exquisite selectivity for benzylic amines enables oxidative self-sorting within dynamic mixtures of amines and imines to afford high yields of cross-coupled imine products.

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