Functional Calixarenes Active KOH-catalyzed Formation Of C(P)-Te Bond

Calixarenes have become the third generation of supramolecular compounds after crown ethers and cyclodextrins, because of the advantages of flexible cavity structure and diverse conformation. Calixarenes are also easy to be modified by introducing functional groups in the up and down rims, which make the calixarenes present unique ability as needed. Strong interaction was observed between calixarenes and cation oions, maily due to the strong interaction between cation oions and benzene rings and oxygen atom. The calixarenes can activate the nucleophilicity of the negative ions, which promote the reaction efficiently. In this paper, calix[4]arene 1 was used as an activator to activate the catalytic ability of KOH for formation of C(P)-Te.(1) We use the reaction of o,o-diethylphosphonates and diphenyl ditelluride as modle raction to optimize the reaction conditions. After systematic expioring the effections of PTC, solvent, temperature and reaction time to the reaction, the optimal conditions are as follow:calix[4]arene 1(10 mol%), KOH(20 mol%), at rt in THF for 8 h. The reaction scopes of o,o-dialkylphosphonates and diaryl ditellurides are also examined. The results show that all reactions offord the corresponding prodects in the yields of 73%-88% under the optimal conditions.(2) We use the reaction of phenylacetylene and diphenyl ditelluride as modle raction to optimize the reaction conditions. After systematic expioring the effections of PTC, solvent, temperature and reaction time to the reaction, the optimal conditions are as follow:calix[4]arene 1 (10 mol%), KOH(20 mol%), at rt in THF for 10 h. The reaction scopes of terminal alkynes and diaryl ditellurides are also examined. The results show that all reactions offord the corresponding prodects in the yields of 76%-90% under the optimal conditions.Calix[4]arene 1 and target compounds were characterized and confirmed by 1HNMR?13CNMR spectras and mass spectra.