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Direct Dehydroxylative Coupling Reaction of Alcohols with Organosilanes through Si-X Bond Activation by Halogen Bonding

Masato Saito, Nobuya Tsuji, Yusuke Kobayashi and Yoshiji Takemoto*

*Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan, Email: takemotopharm.kyoto-u.ac.jp

M. Saito, N. Tsuji, Y. Kobayashi, Y. Takemoto, Org. Lett., 2015, 17, 3000-3003.

DOI: 10.1021/acs.orglett.5b01290



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Abstract

The combination of a halogen bond donor with trimethylsilyl halide is an efficient cocatalytic system for a direct dehydroxylative coupling reaction of alcohol with various nucleophiles, such as allyltrimethylsilane and trimethylcyanide, to give the corresponding adduct in moderate to excellent yields.

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Key Words

benzylation, allylation


ID: J54-Y2015