Coordination-Induced Migration of Aryl Groups in the Reactions of a Dialkylsilanone with a Series of Triarylboranes

Abstract

Although carbonyl compounds are activated by the coordination of a Lewis acid to the carbonyl oxygen atom, a similar activation process of R₂ Si=O species remains unclear. We report herein the reactions of a silanone (1, Scheme 1) with a series of triarylboranes to afford the corresponding boroxysilanes. Experimental results and computational studies indicate that the electrophilicity of the unsaturated silicon atom is enhanced by the complexation of 1 with triarylboranes, and the subsequent aryl migration from the boron atom to the electrophilic silicon atom proceeds.

Keywords: Boranes; Lewis acid; Rearrangement; Silanones; Silicon.