Copper-catalyzed C-S Bond Formation For The Synthesis Of S-heterocyclic Compounds

Copper-catalyzed coupling reaction plays an important role in C-Sbonds formation, C-S bonds can be commonly found in numerousbiological and pharmaceutical coumpounds. Due to the unique physicaland chemical properties, trifluoromethyl group can enhance the biologicalactivities of medicines. Thus synthesis of S-heterocyclic compounds witha trifluoromethyl group has received considerable attention in syntheticchemistry. This thesis is going to explore copper-catalyzed couplingreaction for the synthesis of S-containing compounds and S-heterocycliccompounds with a trifluoromethyl group, which is significant in drugdesign and synthesis. The main contents include:(1) Recent advances inthe synthesis of cyanamide and trifluoromethyl compounds, and theformation of C-N bonds and C-S bonds. Their applications in organicsynthesis are also described.(2) Copper-catalyzed tandem reaction of2-iodophenyl isothiocyanateswith aryl iodides and aqueous ammonia is developed, which leads to thesynthesis of2-(arylthio)aryl cyanamides by sequently formation of C-Nbond and C-S bond.(3) A copper-catalyzed regio-and stereoselective6-exo-digcyclization of1-chloro-1,5-enynes with sodium hydrosulfide has beendeveloped. In the presence of CuI and t-BuONa, a variety of(Z)-1-methylene-3-trifluoromethyl-1H-isothiochromenes were preparedin moderate to good yields.