Iridium-Catalyzed meta -Selective C–H Silylation of Arenes Enabled by Remote Regiocontrol with a Spirobipyridine Ligand

Organosilicon derivatives are important compounds in industry and valuable synthetic intermediates in organic synthesis. Direct introduction of the silicon functionality is an attractive, straightforward synthetic approach to these compounds; however, previously reported catalytic silylation of arenes has suffered from poor site-selectivity. We report that an iridium catalyst in combination with a spirobipyridine ligand selectively silylates mono- and disubstituted arenes at the meta position relative to the larger substituent. The catalyst recognizes the shape of the organic substrate through remote steric interactions to control the site-selectivity, applicable to a variety of functional groups.