Bis(difluoromethyl)trimethylsilicate Anion: A Key Intermediate in Nucleophilic Difluoromethylation of Enolizable Ketones with Me<sub>3</sub>SiCF<sub>2</sub>H
Dingben Chen(Chinese Academy of Sciences), Chuanfa Ni(Chinese Academy of Sciences), Yanchuan Zhao(Chinese Academy of Sciences), Xian Cai(Chinese Academy of Sciences), Xinjin Li(Chinese Academy of Sciences), Pan Xiao(Chinese Academy of Sciences), Jinbo Hu(Chinese Academy of Sciences)
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Abstract
A pentacoordinate bis(difluoromethyl)silicate anion, [Me3 Si(CF2 H)2 ](-) , is observed for the first time by the activation of Me3 SiCF2 H with a nucleophilic alkali-metal salt and 18-crown-6. Further study on its reactivity by tuning the countercation effect led to the discovery and development of an efficient, catalytic nucleophilic difluoromethylation of enolizable ketones with Me3 SiCF2 H by using a combination of CsF and 18-crown-6 as the initiation system. Mechanistic investigations demonstrate that [(18-crown-6)Cs](+) [Me3 Si(CF2 H)2 ](-) is a key intermediate in this catalytic reaction.
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