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Communication | Special issue | Vol 90, No. 2, 2015, pp.907-917
Published online, 4th November, 2014
DOI: 10.3987/COM-14-S(K)105
Theoretical Study on Radical Trifluoromethylation of Silyl Enol Ethers Accelerated via Complexation with Dialkylzinc

Susumu Kawauchi, Yoshihiro Hayashi, Yuichi Tomita, Ryota Hashimoto, Kazuya Honda, Yoshimitsu Itoh, and Koichi Mikami*

*Department of Applied Chemistry, Graduate School of Science and Technology, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan


Theoretical study on the electrophilic radical trifluoromethylation of silyl enol ethers is reported to give α-trifluoromethyl carbonyl compounds; the complexation with dialkylzinc accelerates the radical addition of highly electrophilic trifluoromethyl radical to silyl enol ethers via the Zn-π complex (A) rather than the Zn-O complex (B).