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Metal‐Free Cycloaddition of Epoxides and Carbon Dioxide Catalyzed by Triazole‐Bridged Bisphenol
ChemCatChem ( IF 4.5 ) Pub Date : 2020-05-25 , DOI: 10.1002/cctc.202000508
Yanhong Hao 1 , Dan Yuan 1 , Yingming Yao 1
Affiliation  

1,2,3‐triazole‐bridged bisphenol has been developed as organocatalyst in the coupling of CO2 and epoxides. In the absence of halide co‐catalyst, halomethyl‐substituted epoxides reacted with 1 bar CO2, while a series of aryl‐substituted epoxides were transformed into cyclic carbonates in 57–95 % yields at 120 °C and 10 bar pressure. 1,2,3‐triazole‐bridged bisphenol is thus among the most efficient organocatalysts that are active in the absence of both metal and halide. For alkyl‐substituted epoxides, good yields of 80–95 % were obtained under 1 bar CO2 in the presence of halide. The bisphenol was recycled 14 times in the presence of halide, and 5 times in the absence of halide. The two hydroxyl groups of bisphenol are proposed to work synergistically in the catalytic cycle.

中文翻译:

三唑桥连双酚催化的环氧和二氧化碳的无金属环加成反应

1,2,3-三唑桥连双酚已被开发为在CO 2和环氧化物偶联中的有机催化剂。在没有卤化物助催化剂的情况下,卤甲基取代的环氧化物与1 bar CO 2反应,而一系列芳基取代的环氧化物在120°C和10 bar压力下以57–95%的产率转化为环状碳酸酯。因此,1,2,3-三唑桥连的双酚是最有效的有机催化剂,在没有金属和卤化物的情况下具有活性。对于烷基取代的环氧化物,在1 bar CO 2下获得良好的收率80-95%在卤化物的存在下。在存在卤化物的情况下,双酚被循环14次,在不存在卤化物的情况下被循环5次。提出双酚的两个羟基在催化循环中协同作用。
更新日期:2020-05-25
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