| 3-sulfur (selenium)-multi-substituted indole and benzofuran derivatives are widely present in fields of biology, pharmaceuticals, pesticide, and dye stuff and so on. Based on copper-catalyzed coupling reactions sonogashira series is one of the important means to build such compounds, especially since the 1990s, with the legends and catalyst combination of catalytic systems development, simple and efficient synthesis of nitrogen, oxygen miscellaneous ring compound into a new hot spot sonogashira reaction studies.In the second chapter, we use substituted ortho derivatives with terminal alkynes, disulfide or diselenide to carry on the coupling, reactions were carried out under anhydrous and anaerobic conditions by one-pot, The effect of variables including catalyst, additive, solvent, base, and temperature on the template reaction of N-(2-bromophenyl)-2,2,2-trifluoroacetamide with phenyl acetylene, disulfide, we investigated has been studied, and the optimum cross-coupling condition is determined:30% L-proline,10% Cul,200% Cs2CO3, DMF, N2,100℃,24 h. After that, the scope of reaction is studied. And the result is satisfactory, that aryl halides can react with terminal alkynes, disulfide or diselenide under a gentle condition. The results are all excellent whether the substrates withelectron-withdrawing group or electron-donating group.In the third chapter, we use Substituted o-indophenols with terminal alkynes, disulfide or diselenide to carry on the coupling, reactions were carried out under anhydrous and anaerobic conditions, The effect of variables including catalyst, additive, solvent, and temperature on the template reaction of 2-iodophenol with phenyl acetylene, disulfide, we investigated has been studied, and the optimum cross-coupling condition is determined:30% L-proline,10% Cul,200% Cs2CO3, DMSO, N2,90-100℃,20 h. Then, we examined the response of universality, the results show that o-iodine phenol with different substituents can react with terminal alkynes, disulfide or diselenide under a gentle condition. The yield of the target products were75%-89%. |
