Synthesis of α-trifluoromethylstyrene derivatives via Ni-catalyzed cross-coupling of 2-bromo-3,3,3-trifluoropropene and aryl Grignard reagents

The Ni-catalyzed cross-coupling of 2-bromo-3,3,3-trifluoropropene and aryl Grignard reagents was investigated. When NiCl2(PPh3)2 was used as a catalyst, the highest yield of α-trifluoromethylstyrene (89%) from 2-bromo-3,3,3-trifluoropropene and PhMgBr was obtained in 1,3-dimethyl-2-imidazolidinone at 50 °C for 30 min. Various α-trifluoromethylstyrene derivatives could be produced in satisfactory yields by NiCl2(PPh3)2-catalyzed coupling using aryl Grignard reagents.

Graphical abstractThe Ni-catalyzed cross-coupling of 2-bromo-3,3,3-trifluoropropene (1) and aryl Grignard reagents was investigated. NiCl2(PPh3)2 showed the highest activity in the coupling of 1 and phenylmagnesium bromide providing α-trifluoromethylstyrene (89%) in 1,3-dimethyl-2-imidazolidinone at 50 °C for 30 min. Various α-trifluoromethylstyrene derivatives could be produced in satisfactory yields by NiCl2(PPh3)2-catalyzed coupling using aryl Grignard reagents.Figure optionsDownload full-size imageDownload as PowerPoint slide