Organofluorine Chemistry
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Congratulations to Dr. Dingben Chen, on having published an Angew. Chem. paper!
Date:2016/9/8

Bis(difluoromethyl)trimethylsilicate Anion: A Key Intermediate in Nucleophilic Difluoromethylation of Enolizable Ketones with Me3SiCF2H 
Chen, Dingben; Ni, Chuanfa; Zhao, Yanchuan; Cai, Xian; Li, Xinjin; Xiao, Pan; Hu, Jinbo*
Angew. Chem., Int. Ed. 2016, 55, 12632 – 12636.
 

 

Abstract:

       A pentacoordinate bis(difluoromethyl)silicate anion, [Me3Si(CF2H)2]-, is observed for the first time by the activation of Me3SiCF2H 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 Me3SiCF2H by using a combination of CsF and 18-crown-6 as the initiation system. Mechanistic investigations demonstrate that [(18-crown-6)Cs]+[Me3Si(CF2H)2]- is a key intermediate in this catalytic reaction.






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