N-Heterocyclic Silylene Coordinated Dialkyl Borenium Equivalent

In an attempt to prepare the heavier analogue of NHC-stabilized borenium cation, we have prepared a silylene-coordinated borenium equivalent (1a), which can be viewed as a contact ion pair of borenium and triflate. The triflate anion coordinates to the oxophilic silicon center, leaving the boron center existing in a trigonal-planar geometry in the solid state and in solution. Nucleophilic substitution reactions of 1a all result in the release of free silylene ligand, demonstrating the borenium-ion-like reactivity of 1a. Chemical reduction of 1a leads to a neutral radical possessing a partial Si–B double bond.