| Title | Facile difluoromethylation of aliphatic alcohols with an S-(difluoro-methyl)sulfonium salt: reaction, scope and mechanistic study |
| Authors | Liu, Guo-Kai Li, Xin Qin, Wen-Bing Peng, Xiao-Shui Wong, Henry N. C. Zhang, Linxing Zhang, Xinhao |
| Affiliation | Shenzhen Univ, Hlth Sci Ctr, Sch Pharmaceut Sci, 3688 Nanhai Ave, Shenzhen 518060, Peoples R China Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China Peking Univ, Shenzhen Grad Sch, State Key Lab Chem Oncogen, Lab Computat Chem & Drug Design, Shenzhen 518055, Peoples R China |
| Issue Date | 2019 |
| Publisher | CHEMICAL COMMUNICATIONS |
| Abstract | A facile and practical approach for the difluoromethylation of aliphatic alcohols with an S-(difluoromethyl)sulfonium salt was developed. A wide variety of alcohols with broad functional groups are compatible to furnish the corresponding alkyl difluoromethyl ethers in good to excellent yields under mild reaction conditions. Control experiments and DFT computational studies suggest that the difluoromethylation of alcohols mainly proceeds via a difluorocarbene pathway involving a five-membered transition state with the participation of water, whose crucial role in this reaction was also elucidated by control experiments. |
| URI | http://hdl.handle.net/20.500.11897/543521 |
| ISSN | 1359-7345 |
| DOI | 10.1039/c9cc03487k |
| Indexed | CCR IC SCI(E) EI |
| Appears in Collections: | 深圳研究生院待认领 |
