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Development of (Trifluoromethyl)zinc Reagent as Trifluoromethyl Anion and Difluorocarbene Sources

Kohsuke Aikawa, Wataru Toya, Yuzo Nakamura and Koichi Mikami*

*Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8552, Japan, Email: mikami.k.abm.titech.ac.jp

K. Aikawa, W. Toya, Y. Nakamura, K. Mikami, Org. Lett., 2015, 17, 4966-4999.

DOI: 10.1021/acs.orglett.5b02439 (free Supporting Information)


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Abstract

A stable (trifluoromethyl)zinc reagent can be generated from CF3I and ZnEt2. Trifluoromethylation of carbonyl compounds proceeds smoothly with diamine as a ligand and ammonium salt as an initiator. Moreover, the (trifluoromethyl)zinc reagent can also be employed as a difluorocarbene source for gem-difluoroolefination of carbonyl compounds as well as gem-difluorocyclization of alkenes or alkynes.

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Key Words

trifluoromethyl carbinols


ID: J54-Y2015