Hydrosilylation of Carbonyl Compounds Catalyzed through a Lithiated Hydrazone Derivative

TitleHydrosilylation of Carbonyl Compounds Catalyzed through a Lithiated Hydrazone Derivative
Publication TypeJournal Article
Year of Publication2018
AuthorsRaya-Barón Á, Oña-Burgos P, Rodríguez-Diéguez A, Fernandez I

A well-defined lithiated hydrazone derivative has been synthesized and fully characterized through various analytical platforms, including multinuclear (1H, 13C, 15N, 7Li) and two-dimensional NMR, high-resolution MS spectrometry, IR, and X-ray diffraction crystallography. It behaves as a binuclear species in the solid state and as a monomeric contact ion pair in solution. It has also been tested as a catalyst in hydrosilylation reactions, being the first lithium hydrazone reported to catalyze the full conversion of carbonyls of different nature into alcohols in short reaction times, at room temperature, and with catalyst loadings equal to or below 0.5 mol %. Kinetic studies have proven fractional order dependences with respect to ketone and silane and first order dependence in the case of the catalyst. The proposed reaction mechanism is characterized by the nucleophilic addition of the lithium hydrazonide to the silicon atom of the silane to give a five-coordinate silicon species.

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