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Metal‐Free Cycloaddition of Epoxides and Carbon Dioxide Catalyzed by Triazole‐Bridged Bisphenol
Author(s) -
Hao Yanhong,
Yuan Dan,
Yao Yingming
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202000508
Subject(s) - halide , chemistry , catalysis , bisphenol a , bisphenol , alkyl , cycloaddition , aryl , organic chemistry , polymer chemistry , medicinal chemistry , epoxy
1,2,3‐triazole‐bridged bisphenol has been developed as organocatalyst in the coupling of CO 2 and epoxides. In the absence of halide co‐catalyst, halomethyl‐substituted epoxides reacted with 1 bar CO 2 , 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 CO 2 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.