1,6-Nucleophilic Di- and Trifluoromethylation of <i>para</i>-Quinone Methides with Me<sub>3</sub>SiCF<sub>2</sub>H/Me<sub>3</sub>SiCF<sub>3</sub> Facilitated by CsF/18-Crown-6
Dingben Chen,
Ling Huang,
Mingyu Liang,
Xiaojing Chen,
Dongdong Cao,
Pan Xiao,
Chuanfa Ni,
Jinbo Hu
Affiliations
Dingben Chen
School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China
Ling Huang
School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China
Mingyu Liang
School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China
Xiaojing Chen
School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China
Dongdong Cao
School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China
Pan Xiao
Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
Chuanfa Ni
Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
Jinbo Hu
Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
The direct 1,6-nucleophilic difluoromethylation, trifluoromethylation, and difluoroalkylation of para-quinone methides (p-QMs) with Me3SiRf (Rf = CF2H, CF3, CF2CF3, CF2COOEt, and CF2SPh) under mild conditions are described. Although Me3SiCF2H shows lower reactivity than Me3SiCF3, it can react with p-QMs promoted by CsF/18-Crown-6 to give structurally diverse difluoromethyl products in good yields. The products can then be further converted into fluoroalkylated para-quinone methides and α-fluoroalkylated diarylmethanes.
