The Research On Oxidation Of α-Bromoacetophenone And Its Derivative Via Electrochemical Method

Organic electrochemistry is the subject that integrated with organic synthesis and electrochemical technology. Recently, as the more paying to protect the environment of the world, the conception of ’Green Chemistry’ is appeared. Green chemistry is also called environment-friednly chemistry, clean chemistry and sustainable technology. Using of clean electronics instead of the traditional oxidants and reducing agents are the most feature of organic electrochemistry. In addition, organic electrochemistry is famous as reducing the material consumption in the source, highly selectivity, easily to control. The reaction conditions are mild. It usually reactes at room temperature and pressure. By adjusting the electrolysis conditions, the process can be more easily controlled. It gives more accordence with the requirements of low carbon economy and sustainable development.α-Carbonyl amides and α - carbonyl esters play more important role in intermediating of drugs. In this paper, the electrochemical oxidation of a-bromoacetophenone derivatives with primary amines and secondary amines were carried out. The reaction was processed with KI as catalyst, adding 4- nitrophenol as the auxiliary agent in the solvent of methanol at a single cell. The electrolysis is carried out using Pt sheet as working electrode and auxiliary electrode. Under the constant current condition, a-bromoacetophenone reactes with the primary amine generated a series of amide compounds. Interestingly, when a-bromoacetophenone reactes with the secondry amine in the same experimental condition,the product does not generate the a-carbonyl amide, but the a-carbonyl esters instead. In this paper, nine compounds were synthesized of a-carbony amide and a-carbony ester respectively. The reaction mechanism were discussed preliminarily. And the resulting products were characterized by 1H NMR and 13C NMR.In summary,we successfully developed the new methods to form carbonyl,amine and ester functional groups by organic electrochemical synthesis. The reaction system has a wide applicability of the substrates and highly efficiency. Compared with the traditional chemical methods, this method is more green. The operation is simple. Organic electrochemistry method provides a new direction for the green organic synthesis.