Borylation and Silylation of C–H Bonds: A Platform for Diverse C–H Bond Functionalizations

Methods that functionalize C–H bonds can lead to new approaches for the synthesis of organic molecules, but to achieve this goal, researchers must develop site-selective reactions that override the inherent reactivity of the substrates. Moreover, reactions are needed that occur with high turnover numbers and with high tolerance for functional groups if the C–H bond functionalization is to be applied to the synthesis of medicines or materials. This Account describes the discovery and development of the C–H bond functionalization of aliphatic and aromatic C–H bonds with borane and silane reagents. The fundamental principles that govern the reactivity of intermediates containing metal–boron bonds are emphasized and how an understanding of the effects of the ligands on this reactivity led us to broaden the scope of main group reagents that react under mild conditions to generate synthetically useful organosilanes is described. Read more on publisher's site.