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

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.