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35.1.1.5.13.12 Method 12: Chlorodehydroxylation with Chlorodimethylsilane

DOI: 10.1055/sos-SD-135-00009

Margaretha, P.Science of Synthesis Knowledge Updates, (20142439.

Dialkylchlorosilanes commonly react with alcohols in the presence of a catalyst to afford the corresponding (reduced) hydrocarbons and hydrogen chloride. It has recently been shown that under appropriate reaction conditions, alcohols 46 can be converted by the same reagent into chloroalkanes 47 with concomitant evolution of molecular hydrogen. Both indium(III) chloride in the presence of benzil[‌36‌,‌37‌] and gallium(III) chloride in the presence of diethyl tartrate (DET)[‌38‌] allow the efficient conversion of alcohols into chlo­roalkanes using chlorodimethylsilane (Scheme 19). High selectivities for tertiary alcohols over primary alcohols are observed in these reactions.

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