Chen Xia, Liu Yining, Zhang Sheng, Li Yang, Zhou Xiao-Yu, Feng Xiujuan, Yu Xiaoqiang, Yamamoto Yoshinori, Bao Ming
State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China.
School of Chemistry and Materials Engineering, Liupanshui Normal University, Liupanshui 553004, China.
Org Lett. 2024 Aug 30;26(34):7233-7238. doi: 10.1021/acs.orglett.4c02689. Epub 2024 Aug 19.
A new trifluoroacetylation reagent was developed by using inexpensive and readily available trifluoroacetic anhydride and -phenyl-4-methylbenzenesulfonamide for the first time. The reaction of (het)aryl boronic acids with the new trifluoroacetylation reagent, -phenyl--tosyltrifluoroacetamide, proceeded smoothly in the presence of a palladium catalyst to provide trifluoromethyl ketones in satisfactory to excellent yields. Various groups, including the synthetically useful functional groups Cl, TMS, and PhCO, were tolerated well under the current reaction conditions. This new trifluoroacetylation reagent can be used in the large-scale synthesis of trifluoromethyl ketones, even at a low palladium catalyst loading.
