Chemoselective organocatalytic aerobic oxidation of primary amines to secondary imines

Org Lett. 2012 Jun 1;14(11):2850-3. doi: 10.1021/ol301095j. Epub 2012 May 17.


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.