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      Chemoselective Organocatalytic Aerobic Oxidation of Primary Amines to Secondary Imines

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      Organic Letters
      American Chemical Society (ACS)

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          Abstract

          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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          Author and article information

          Journal
          Organic Letters
          Org. Lett.
          American Chemical Society (ACS)
          1523-7060
          1523-7052
          May 22 2012
          May 17 2012
          : 14
          : 11
          : 2850-2853
          Article
          10.1021/ol301095j
          22594886
          fbaa3e35-63ab-4db6-91b4-9cf2566f2357
          © 2012
          History

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