Abstract
The synthesis of 4'-nonafluorobutylacetophenone by metal-assisted cross-coupling reaction of 1-iodo-perfluorobutane and 4'-bromoacetophenone was presented. The effect of metal (iron, copper), metal salt (copper(I) bromide, copper(II) chloride), ligand (2,2'-bipyridine, N,N,N',N'',N''',N'''-hexamethyltriethylenetetramine, N,N,N',N'',N''-pentamethyldiethylenetriamine), and solvent (N,N dimethylformamide, dimethylsulfoxide) was studied in order to elucidate their role in the optimization of the reaction conditions. The best conditions were found for the reaction involving copper as the catalyst, 2,2-bipyridine as the ligand in presence of N,N-dimethylformamide as the solvent that led to 73% yield of the desired product (for quantitative conversions of both 1-iodoperfluorobutane and 4'-bromoacetophenone). All compounds were identified by 1H NMR and 19F NMR spectroscopy.