A Base-Stabilized Silylene-Promoted C(sp3)−H Borylation and H2 Activation

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

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Original languageEnglish
Pages (from-to)9551–9559
Journal / PublicationInorganic Chemistry
Volume59
Issue number14
Online published25 Jun 2020
Publication statusPublished - 20 Jul 2020

Abstract

Treatment of the amidinato amidosilylene [L{(Me3Si)2N}Si:] [1, L = PhC(NtBu)2] with a slight excess of borane–tetrahydrofuran complex [BH3·THF] in toluene at room temperature afforded the silylene–borane adduct [L{(Me3Si)2N}Si:→BH3] (2). A triflate substituent was introduced on the boron center by reacting 2 with methyl triflate [MeOTf] (OTf = OSO2CF3) in toluene at room temperature to form [L{(Me3Si)2N}Si:→BH2OTf] (3), with the elimination of CH4 gas. The intramolecular C(sp3)–H borylation and H2 elimination occurred by reacting complex 3 with 1 in refluxing toluene to form a C–B bond in the resulting silylene–boronium ion 5. Complex 5 activated H2 gas or NH3BH3 at room temperature to form silylene–borane adduct 2 and [L{(Me3Si)2N}Si-H]OTf. Additionally, the reaction of 5 with H2 was studied through density functional theory calculations.

Citation Format(s)

A Base-Stabilized Silylene-Promoted C(sp3)−H Borylation and H2 Activation. / Khoo, Sabrina; Siu, Chi-Kit; So, Cheuk-Wai.

In: Inorganic Chemistry, Vol. 59, No. 14, 20.07.2020, p. 9551–9559.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review