Synthesis of α-trifluoromethylstyrene derivatives via Pd-catalyzed cross-coupling of 2-bromo-3,3,3-trifluoropropene and arylmagnesium bromides

Pd-catalyzed cross-coupling of 2-bromo-3,3,3-trifluoropropene (BTP) and arylmagnesium bromides was investigated. Diphenylphosphinomethane (dppm) was exclusively effective in the coupling among the phosphine ligands tested with Pd(0) and Pd(II) complexes. The use of diphenylphosphinomethane-coordinated Pd(II) complex, PdCl2(dppm), resulted in the highest yield of α-trifluoromethylstyrene (98%) from 2-bromo-3,3,3-trifluoropropene and phenylmagnesium bromide in 1,4-dioxane solvent at 50 °C for 30 min. The PdCl2(dppm)-catalyzed coupling could be applied to the synthesis of α-trifluoromethylstyrene derivatives with satisfactory yields using arylmagnesium bromides.

Graphical abstractThe Pd-catalyzed cross-coupling of 2-bromo-3,3,3-trifluoropropene and arylmagnesium bromides was investigated. PdCl2(dppm) gave the highest yield of α-trifluoromethylstyrene (98%) from 2-bromo-3,3,3-trifluoropropene and phenylmagnesium bromide in 1,4-dioxane solvent. This PdCl2(dppm)-catalyzed coupling could be applied to the synthesis of α-trifluoromethylstyrene derivatives in satisfactory yields using some arylmagnesium bromides.Figure optionsDownload full-size imageDownload as PowerPoint slide