Visible Light Induced Rhodium(I)-Catalyzed C-H Borylation

Abstract

An efficient visible light induced rhodium(I)-catalyzed regioselective borylation of aromatic C-H bonds is reported. The photocatalytic system is based on a single NHC-Rh^I complex capable of both harvesting visible light and enabling the bond breaking/forming at room temperature. The chelating nature of the NHC-carboxylate ligand was critical to ensure the stability of the Rh^I complex and to provide excellent photocatalytic activities. Experimental mechanistic studies evidenced a photooxidative ortho C-H bond addition upon irradiation with blue LEDs, leading to a cyclometalated Rh^III -hydride intermediate.

Keywords: C−H activation; boron; carbenes; photochemistry; rhodium.