Received July 15, 2006

Abstract:

Reaction methodology for intermolecular C-H amination of benzylic and 3 C-H bonds is described. This process uses the starting alkane as the limiting reagent, gives optically pure tetrasubstituted amines through stereospecific insertion into enantiomeric 3 centers, displays high chemoselectivity for benzylic oxidation, and enables the facile preparation of isotopically enriched ¹⁵N-labeled compounds. Access to substituted amines, amino alcohols, and diamines is thereby made possible in a single transformation. Important information relevant to understanding the initial steps in the catalytic cycle, reaction chemoselectivity, the nature of the active oxidant, and pathways for catalyst inactivation has been gained through mechanistic analysis; these studies are also presented.

Download the full text: PDF | HTML