Applation Of Diaryliodonium Salts In Organic Syntheses

Hypervalent iodine has recently received considerable attention as a mild, low toxic, and selective reagent in organic synthesis chemistry. Iodine(V) reagents, such as Dess-Martin periodinane and IBX(2-iodoxybenzoic acid), are frequently used as mild oxidants in total syntheses of natural products. Iodine(III) compounds are employed in oxidations of alcohols, alkenes, and a-functionalization of carbonyl compounds. Particular, diaryliodonium salts were involved in many reactions under mild reaction conditions, with good functional groups tolerance and region selectivity.Moreover, it can be reacted with a variety of nucleophile, and used as an arylation reagent.Arylureas and indoles widely exist in natural products and bioactive molecules and have been applied in dyes, pharmaceutics, and chemical industrial. In particular, some arylureas have been shown a marked inhibiting effect on HIV protease enzyme.Traditional methods of synthesis of aryl urea using toxic phosgene and its derivatives,are likely to cause pollution. Meanwhile, the storage of raw materials was not conducive. Carbon monoxide and carbon dioxide, which were used for synthesis of aryl urea, was limited in universal substrates. However, requirement of transition metals, such as palladium, and rhodium, results in high cost in industries. In this thesis, an efficient “one-pot” approach to multiple substituted ureas fromN-arylcyanamide and diaryliodonium salts has been presented under catalyzed by Cu.Compared to the traditional methods, it benefits to the environment. The weak base-promoted chemoselective arylation of secondary amines with diaryliodonium and Cu-catalyzed nucleophilic addition of N-arylcyanamide with second diaryliodonium were involved in this procedure.In this thesis, 1,2-diphenylindole were obtained by diaryliodonium salts and2-alkynylanilines in tert-Bu OH without transition metals. Compared to the traditional methods, the procedure involved no metal-catalyst, mild conditions, and less harmful to the environment. More important, adding the Pd-catalyst, 3,3'-diindolylmethane was obtained by 1,2-diphenyliodole and dimethyl sulfoxide. This method enhance the applation of 1,2-diphenyl to the industry.