Organic Chemistry

Formal gamma-C(sp3)–H Activation of Ketones via Microwave-Promoted and Iminyl-Radical-Mediated 1,5-Hydrogen Atom Transfer



Microwave irradiation of O-phenyloximes triggers N–O homolysis and 1,5-hydrogen atom transfer (HAT), resulting in formal gamma-C–H functionalization of ketones after trapping of the radical intermediate and in situ imine hydrolysis. The Lewis acid InCl3∙H2O facilitated the HAT step, enabling functionalization of nonbenzylic 1° carbon atoms. Both C–O and C–C bond formation could be accomplished by this method.


Thumbnail image of Iminyl Rad C-H activation preprint.pdf