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CO 2 Adducts of α‐Carbon Alkylated N‐Heterocyclic Olefins: Highly Active Organocatalysts for CO 2 Chemical Transformation
Author(s) -
Zhou Hui,
Wang GuoXu,
Lu XiaoBing
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700152
Subject(s) - chemistry , adduct , alkylation , carbon fibers , thermal stability , stereoselectivity , medicinal chemistry , organic chemistry , catalysis , materials science , composite number , composite material
A series of CO 2 adducts of α‐carbon alkylated N‐heterocyclic olefins (ANHOs–CO 2 ) were synthesized and characterized by single‐crystal X‐ray diffraction analysis. The in situ FTIR studies demonstrated that ANHOs–CO 2 adducts showed higher thermal stability than the previously reported α‐carbon nonsubstituted N‐heterocyclic olefins (HNHOs–CO 2 ) due to the enhancement of the electron‐donating properties. Moreover, ANHOs–CO 2 adducts exhibit higher activity in catalyzing the carboxylative cyclization of CO 2 with propargylic alcohols than HNHOs–CO 2 under the same experimental conditions. Meanwhile, various internal and terminal functionalized propargylic alcohols could be tolerated to obtain the corresponding α‐alkylidene cyclic carbonates in moderate to good yields with high stereoselectivity.