In biologically active molecules amine and amide functional groups are ubiquitous. They are often designed into modern drugs as a way to increase their water solubility and improve their pharmacokinetic profile.  A novel intermolecular oxidative amination reaction   that proceeds via oxidative cross-coupling of carbon-hydrogen (C�H) and nitrogen�hydrogen (N�H) bonds to form carbon�nitrogen (C�N) bonds has been  developed which is mediated by an I(III) oxidant and contains no metal catalysts.  The ability to directly form a Caryl-N bond from substrates containing C-H and N-H bonds is a highly desirable process. This rapid and green method proceeds via nucleophilic attack of phthalimide on an aromatic radical cation and can be used to synthesize protected anilines from simple arenes and phthalimide. The future efforts in this project will focus on oxidative amination of olefins and sp3 hybridized carbon-hydrogen (C-H) bonds.

Metal-free intermolecular oxidative C–N bond formation via tandem C–H and N–H bond functionalization

244th National Meeting (2012)

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