Ortho-quinones are intriguing biomimetic catalysts for aerobic oxidation of amines. Precedents for this reactivity include the oxidation of primary amines to imines; however, the reaction scope is limited to activated (typically benzylic) substrates. This presentation will describe our design strategy for new amine-oxidation catalyst development and the subsequent discovery of a quinone/ZnI2 catalyst system that enables efficient aerobic oxidation of secondary amines. This novel catalyst system has been applied to the synthesis of a variety of biologically-important N-heterocycles under remarkably mild conditions.

Bio-inspired aerobic oxidation of secondary amines and <i>N</i>-heterocycles

246th National Meeting (2013)

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Bio-inspired aerobic oxidation of secondary amines and N-heterocycles