Advances in disilylation reactions to access cis/trans-1,2-disilylated and gem-disilylated alkenes

Abstract

Organosilane compounds are widely used in both organic synthesis and materials science. Particularly, 1,2-disilylated and gem-disilylated alkenes, characterized by a carbon–carbon double bond and multiple silyl groups, exhibit significant potential for subsequently diverse transformations. The versatility of these compounds renders them highly promising for applications in materials, enabling them to be valuable and versatile building blocks in organic synthesis. This review provides a comprehensive summary of methods for the preparation of cis/trans-1,2-disilylated and gem-disilylated alkenes. Despite notable advancements in this field, certain limitations persist, including challenges related to regioselectivity in the incorporation and chemoselectivity in the transformation of two nearly identical silyl groups. The primary objective of this review is to outline synthetic methodologies for the generation of these alkenes through disilylation reactions, employing silicon reagents, specifically disilanes, hydrosilanes, and silylborane reagents. The review places particular emphasis on investigating the practical applications of the C–Si bond of disilylalkenes and delves into an in-depth discussion of reaction mechanisms, particularly those reactions involving the activation of Si–Si, Si–H, and Si–B bonds, as well as the C–Si bond formation.