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. 2015 Jun 19;17(12):3000-3.
doi: 10.1021/acs.orglett.5b01290. Epub 2015 May 28.

Direct Dehydroxylative Coupling Reaction of Alcohols With Organosilanes Through Si-X Bond Activation by Halogen Bonding

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Direct Dehydroxylative Coupling Reaction of Alcohols With Organosilanes Through Si-X Bond Activation by Halogen Bonding

Masato Saito et al. Org Lett. .

Abstract

The combined use of a halogen bond (XB) donor with trimethylsilyl halide was found to be an efficient cocatalytic system for the direct dehydroxylative coupling reaction of alcohol with various nucleophiles, such as allyltrimethylsilane and trimethylcyanide, to give the corresponding adduct in moderate to excellent yields. Detailed control experiments and mechanistic studies revealed that the XB interaction was crucial for the reaction. The application of this coupling reaction is also described.

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