Use of Catalytic Fluoride under Neutral Conditions for Cleaving Silicon–Oxygen Bonds

Abstract

This Article describes the development of conditions for cleaving silicon-oxygen bonds using catalytic quantities of fluoride at neutral pH in mixed organic-aqueous solutions that contain buffer. A variety of silicon protecting groups can be removed under these conditions, which show tolerance for acid- and base-sensitive groups. A modified procedure also is presented using catalytic fluoride in anhydrous dimethyl sulfoxide-methanol, which generates primarily volatile silicon byproducts.