Synthesis and Functionalization of a 1,4-Bis(trimethylsilyl)tetrasila-1,3-diene through the Selective Cleavage of Si(sp2)-Si(sp3) Bonds under Mild Reaction Conditions

Although the oxidative coupling of disilenides, i.e., the disilicon analogues of vinyl anions, represents a promising route to extend the conjugation between Si=Si double bonds, previously reported synthetic routes to disilenides involve strongly reducing conditions. Herein, we report a novel synthetic route to disilenides from stable disilenes via the selective cleavage of Si(sp(2))-Si(sp(3)) bonds under milder reaction conditions. Using this method, a 1,4-bis(trimethylsilyl)tetrasila-1,3-diene (5) was synthesized from the corresponding silyl-substituted disilene. Moreover, Et3Si-substituted tetrasila-1,3-diene 7 was synthesized via tetrasila-1,3-dien-1-ide 6, which is the first example of a functionalized tetrasila-1,3-diene.