Abstract:

In this experiment, the dehydrogenative coupling of p-ethyl anisole and 2-(1-(4-methoxyphenyl)ethyl)-5-phenyl-2H-tetrazole is realized through electro-oxidation to generate C―N bonds and synthesize a benzyl-azolated aromatic product. The reaction is simple, safe, and efficient. It also integrates the experimental exploration of green chemistry concepts and organic synthetic methodology. As an undergraduate teaching experiment, it not only covers the basic operation of various organic experiments, but also includes reaction monitoring, purification, structural characterization, and other important procedures. Using this experimental protocol, micro-class learning, extended exercises on the progress of C―H activation, interesting experiments, as well as effective synergy of theoretical knowledge and synthetic practice are realized. Thus, the comprehensive ability of undergraduates majoring in chemistry and pharmacy to solve complex organic synthesis problems is improved, and the research foundation to nurture chemistry talents is further established.

Key words: Electrochemical oxidation, Dehydrogenative coupling reaction, Azolation, Green chemistry, Teaching experiment