Catalytic Amination of Aryl Halides in Acetonitrile: Optimization and the Effects of Electron Donating and Withdrawing Groups
Aryl amines are of useful to synthetic chemists. They are found in many products today. So, the most efficient synthesis of these compounds was explored. It was recently discovered that acetonitrile could be a useful solvent for reactions coupling aryl halides and aryl amines. The scope of this reaction using acetonitrile is not known so a systematic study was needed. An electron donating (methoxy) and electron-withdrawing (nitro) group were placed at the three positions of the ring of an aryl halide and aryl amine (aniline) while the effect of these groups were explored. Acetonitrile was used as the solvent at reflux, cesium carbonate as the base, PCy2dmab as the ligand, and Pd2dba3 as the palladium source were used for this reaction. There were also comparison reactions run in order to test the utility of acetonitrile against toluene. The results of the project show that acetonitrile works very well for this type of reaction and worked considerably better than toluene in the comparison reactions. Acetonitrile can be used as another solvent for the cross coupling of aryl amines and aryl halides and adds to the list of possible solvents for reactions of this type.