Beilstein Journal of Organic Chemistry | |
Synthesis of trifluoromethyl ketones by nucleophilic trifluoromethylation of esters under a fluoroform/KHMDS/triglyme system | |
Yamato Fujihira1  Makoto Ono1  Norio Shibata1  Yumeng Liang2  Kazuki Hirano2  Takumi Kagawa3  | |
[1] Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-5888, Japan;Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-5888, Japan;Tosoh Finechem Corporation, 4988, Kaiseicho, Shunan, 746-0006, Japan; | |
关键词: fluoroform; greenhouse gas; hfc-23; trifluoromethyl ketones; trifluoromethylation; | |
DOI : 10.3762/bjoc.17.39 | |
来源: DOAJ |
【 摘 要 】
A straightforward method that enables the formation of biologically attractive trifluoromethyl ketones from readily available methyl esters using the potent greenhouse gas fluoroform (HCF3, HFC-23) was developed. The combination of fluoroform and KHMDS in triglyme at −40 °C was effective for this transformation, with good yields as high as 92%. Substrate scope of the trifluoromethylation procedure was explored for aromatic, aliphatic, and conjugated methyl esters. This study presents a straightforward trifluoromethylation process of various methyl esters that convert well to the corresponding trifluoromethyl ketones. The tolerance of various pharmacophores under the reaction conditions was also explored.
【 授权许可】
Unknown