Copper-Catalyzed Carbon–Silicon Bond Formation

Abstract

Organosilanes have become a mainstay in organic synthesis as they can participate in a wide number of reactions where they act as a soft carbon nucleophile. They can engage in coupling reactions where C–C, C–N, C–O, or a variety of other bonds are formed. Furthermore, organosilanes are effective coupling partners in C–H activations. Despite their utility, synthesis of organosilanes typically relies on precious metals such as platinum and palladium. In the past several years, there has been considerable effort to develop new procedures, which rely on inexpensive catalysts such as first-row transition metals. More specifically, copper-catalyzed silylations have undergone significant development in the past decade. Copper-catalyzed silylations generally rely on either a silylborane, silylzinc, or disilane as the silicon source. However, a number of different transformations can be performed with this small set of reagents including conjugate addition, addition to alkynes, allenes, and carbonyls, coupling reactions, and substitutions. Nearly all of these transformations exhibit high levels of diastereoselectivity, regioselectivity, or enantioselectivity, depending on the transformation. Moreover, there is still plenty of room for further development of copper-catalyzed silylations, which should provide an inexpensive alternative to more traditional silylations.