Study On Synthesis Of Aryl Sulfide

Organosulfur compounds are a class of organic compounds. It has been considerable interest due to their wide industrial, agricultural and pharmacal applications and remain a long-term challenge to chemists. This research range is expanding constantly, including organic synthesis chemistry, pharmacology, biochemistry and structure chemistry, etc. It has become the front field with development prospect. Aryl sulfide, which has great prospects in medicine, agriculture, dyes industrial and, functional materials areas and far-reaching influence on human life, has become one of the hottest research fields. However in the synthesis of aryl sulfide fields some complex ligands or low activity reagents are used, and making the cost of synthesis of such compounds higher. So the further study of these compounds has very important significance.Based on the careful consult and summarize of the literature, our work mainly focus on the following three aspects:Firstly, S-Arylation reaction between diaryliodonium salts and the reagent containing S-H bond were carried out.’The reaction of the diaryliodonium salts with 2-mercaptobenzothiazole,2-mercaptobenzimidazole and methyl thiophenol have been developed to produce arylation products. Through the discussion of the effect of different solvents, the reaction time and the reaction temperature, optimal reaction conditions were determined:molar ratio of S-H bond compounds and diaryliodonium was 1:1.2; the reaction was carried out at 130℃, the reaction time was 24h, DMF was used as solvent. In addition, the reaction mechanism was explored by monitoring the reaction using the HPLC technique.Secondly, microwave radiation has been used in C-S coupling reaction. The reaction between 2-mercaptobenzothiazole,2-mercaptobenzimidazole, 4,4’-thiobisbenzenethiol and aryl iodides were carried out. Through the discussion of the effect of different solvents, the reaction time and the reaction temperature, optimal reaction conditions were determined:the amount of CuI was 10mol%; KOH was used as base; the reaction time was 10min, DMF was used as solvent. The structures of products were characterized by 1H NMR,13C NMR. The high efficiency of microwave radiation to the oil bath has been proved by the HPLC technique. In addition, the possible reaction mechanism has been discussed. It may become a high efficient, mild and environmental friendly technique in the synthesize of aryl sulfide.Thirdly, the direct copper-catalyzed C-S coupling reaction of heterocyclic compounds with biphenyl disulfide, using as sulfur source have been developed. The reaction were carried out by biphenyl disulfide and benzothiophene, indole,N-methylindole etc to produce corresponding aryl sulfide compound. Through the discussion of the effect of different solvents, the reaction time and the reaction temperature, optimal reaction conditions were determined:the amount of Cul was 10mol%; the reaction was carried out at 110℃; the reaction time was 12h, DMSO was used as solvent. The possible reaction mechanism has been deduced through the discussion of the structure of benzotriazole compounds.