Direct Difluoromethylation of Alcohols with an Electrophilic Difluoromethylated Sulfonium Ylide.
A general method for the formation of alkyl difluoromethylethers under mild reaction conditions and with good functional-group tolerance was developed. The development of the method was based on the invention of a stable, electrophilic, difluoromethylating reagent, difluoromethyl-(4-nitrophenyl)-bis(carbomethoxy) methylide sulfonium ylide, which was synthesized by reaction of the easily available 4-nitrophenyl (difluoromethyl)thioether and dimethyl diazomalonate in the presence of a rhodium catalyst.
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
Jiansheng
J
Zhu
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
Yafei
Y
Liu
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China. shenql@sioc.ac.cn.
Qilong
Q
Shen
alcohols; fluorine; reaction mechanisms; synthetic methods; ylides