Cp*Rh(<scp>iii</scp>) catalyzed <i>ortho</i>-halogenation of <i>N</i>-nitrosoanilines by solvent-controlled regioselective C–H functionalization

Abstract

We present a novel, efficient, and regioselective method for the rhodium-catalyzed direct C-H ortho-halogenation of anilines that involves a removable N-nitroso directing group. This method featured mild reaction conditions, wide substrate scope, good functional group tolerance and satisfactory yields. To maintain the high ortho-regioselectivity and conversion, increasing the steric hindrance of the solvent was critical. Preliminary mechanistic studies suggest that C-H activation may be involved in the rate-determining step.