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Silylation of Aryl Halides with Monoorganosilanes Activated by Lithium Alkoxide

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journal contribution
posted on 01.05.2018 by Takumi Yoshida, Laurean Ilies, Eiichi Nakamura
Lithium alkoxide activates a monoorganosilane to generate a transient LiH/alkoxysilane complex, which quickly reacts with aryl and alkenyl halides at 25 °C to deliver a diorganosilane product. Experimental and theoretical studies suggest that the reaction includes nucleophilic attack of LiH on the halogen atom of the organic halide to generate a transient organolithium/alkoxysilane intermediate, which undergoes quick carbon–silicon bond formation within the complex.