1628946-75-7Relevant academic research and scientific papers
Nucleophilic difluoromethylation of epoxides with PhSO(NTBS)CF2H by a preorganization strategy
Shen, Xiao,Liu, Qinghe,Luo, Tao,Hu, Jinbo
, p. 6795 - 6800 (2014/06/09)
Unlike the facile synthesis of β-monofluoromethyl alcohols by nucleophilic monofluoromethylation of epoxides, the synthesis of β-difluoromethyl alcohols by nucleophilic difluoromethylation of epoxides still remains a challenge. Herein, studies on tackling this problem with PhSO(NTBS)CF2H (2; TBS=tert-butyldimethylsilyl) are reported. The preorganization of 2 and epoxides with BF3Et2O was found to be crucial for the reaction. The reaction shows excellent regioselectivity and has a broad substrate scope. The facile transformation of the ring-opened products to β-difluoromethyl, γ-difluoromethyl, and β-difluoromethylenyl alcohols demonstrates the synthetic utility of the reaction.
