Study On The Formation Of C - S (C - Se) By Metal - Free Catalytic Oxidation

In recent years, free radical reaction mechanism of catalytic oxidative coupling reaction to construct the new compounds has attracted more and more chemists’ attention. Compared with the cross coupling reaction catalyzed by transition metals, free radical reaction avoid to use the relatively expensive catalyst and more complex reaction system. It is more accord with the atom economy and good selectivity in the synthesis of carbon-carbon and carbon-heteroatom bond. In this thesis, peroxide DTBP and TBHP were used as efficient oxidant and free radical initiator, due to the characteristics of cheap, safe and environment friendly and using disulfides as the substrate to synthetic thiol esters. It includes the following two aspects:1. Benzaldehyde derivatives as the substrate to synthetic thiol estersUse benzaldehyde derivatives as acyl source and react with disulfides in DTBP, which as oxidant and free radical initiator, realizes the rupture of C-H bond and S-S bond and then generate new C-S bond. The method used the benzaldehyde as acyl source, which is inexpensive and low toxicity. And the reaction had a simple synthetic route and easy to operate.2. Benzyl alcohol derivatives as the substrate to synthetic thiol estersUse sulfides as sulfur source and react with benzyl alcohol and in the condition of TBHP to produce thiol esters through oxidative coupling process. The reaction conditions are mild and the raw material were easily available, which consistent with the concept of green chemistry.