Ruthenium(ii)-catalyzed ortho-C–H arylation of diverse N-heterocycles with aryl silanes by exploiting solvent-controlled N-coordination

Abstract

We report the first method for the direct, regioselective Ru(II)-catalyzed oxidative arylation of C–H bonds in diverse N-heterocycles with aryl silanes by exploiting solvent-controlled N-coordination. The reaction takes advantage of the attractive features of organosilanes as coupling partners, providing proof of concept for N-directed Ru(II)-catalyzed C–H arylation. This novel, operationally-simple and versatile protocol utilizes the Ru(II)/CuF₂ reagent system in which CuF₂ serves as a dual activator/oxidant in non-coordinating solvents to accommodate for ligand N-coordination. This first Ru(II)-catalyzed N-directed Hiyama C–H arylation offers broad implications to achieve numerous C–H bond functionalizations by versatile ruthenium(II) catalysis manifold.