The New Oxidative Coupling Reactions Promoted By Diethyl Azodicarboxylate

With the requirement of atom economy and green chemistry concepts, the use of non-metallic reagents in place of traditional metal catalysts has become one of important research focus. Its advantage is not only effectively to avoid use of the metal catalysts, but also to reduce costs and environment pollution.Recently we reported that copper/diethyl azodicarboxylate (DEAD) mediated the regioselective alkynylation of unactivated aliphatic tertiary methylamine with terminal alkyne and diethyl azodicarboxylate promoted dehydrogenation of tertiaryamine and tandem coupling reaction with sulfonyl azide. Based on these, the following researches were discussed.This dissertation contains three parts:The first part mianly described the application of DEAD in organic synthesis such as Mitsunobu reactions, the amination reactions and the Huisgen zwitterion and etc.In the second part, we explored that DEAD promoted the dehydrogenative coupling of N,N-dimethylcyclohexylamine and1,3-dicarbonyl derivatives for the synthesis of methylene-bridged bis-1,3-dicarbonyl derivatives. The reaction has the advantage of high yields and mild reaction conditions.The third part introduced the Glaser coupling reaction of terminal alkynes assisted by DEAD and a catalytic amount of N-methylimidiazole and CuI. This reaction could be completed in short time and given the desired products in high yields and almost no by-products.