A Base-Stabilized Silylene-Promoted C(sp)-H Borylation and H Activation.

Treatment of the amidinato amidosilylene [L{(MeSi)N}Si:] [, L = PhC(NBu)] with a slight excess of borane-tetrahydrofuran complex [BH·THF] in toluene at room temperature afforded the silylene-borane adduct [L{(MeSi)N}Si:→BH] (). A triflate substituent was introduced on the boron center by reacting with methyl triflate [MeOTf] (OTf = OSOCF) in toluene at room temperature to form [L{(MeSi)N}Si:→BHOTf] (), with the elimination of CH gas. The intramolecular C(sp)-H borylation and H elimination occurred by reacting complex with in refluxing toluene to form a C-B bond in the resulting silylene-boronium ion . Complex activated H gas or NHBH at room temperature to form silylene-borane adduct and [L{(MeSi)N}Si-H]OTf. Additionally, the reaction of with H was studied through density functional theory calculations.