Visible-Light-lnduced, Metal-Free Carbene Insertion into B-H Bonds between Acylsilanes and Pinacolborane

摘要

Carbene insertion reactions with B-H bonds are a challenging but promising method for the synthesis of organoboranes. Herein, we report visible light-induced B-H insertions of HBpin with acylsilane. This metal-free and operationally simple reaction proceeds in an atom-economical way with broad substrate scope under mild reaction conditions, affording a variety of important alpha-alkoxyorganoboronate esters in quantitative yields. Control experiments and density functional theory calculations suggest that the siloxycarbene generation from the T-1 state of acylsilane and the carbene insertion into the B-H bond occurred in a concerted manner.