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An Experimental and Theoretical Study on the Unexpected Catalytic Activity of Triethanolamine for the Carboxylative Cyclization of Propargylic Amines with CO 2
Author(s) -
Zhao Yuling,
Qiu Jikuan,
Li Zhiyong,
Wang Huiyong,
Fan Maohong,
Wang Jianji
Publication year - 2017
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201700241
Subject(s) - triethanolamine , chemistry , catalysis , alkanolamine , environmentally friendly , atmospheric pressure , combinatorial chemistry , organic chemistry , analytical chemistry (journal) , ecology , oceanography , aqueous solution , biology , geology
Chemical conversion of CO 2 under atmospheric pressure and metal‐free conditions remains a great challenge. In this work, a series of alkanolamines, low‐cost and biodegradable bases, were used to catalyze the carboxylative cyclization of propargylic amines with CO 2 . Among these alkanolamines, triethanolamine (TEOA) was found to be a highly efficient organocatalyst for this important transformation at atmospheric pressure, and a series of desired products were synthesized in good to excellent yields. After the reactions, TEOA could be easily recovered and reused without obvious reduction in the efficiency. DFT studies revealed that TEOA may activate CO 2 to form a ring‐shaped carbonate intermediate that plays an important role in the catalysis of the reaction. This finding provides an effective and environmentally friendly alternative route for the production of 2‐oxazolidinones.