title: An Experimental and Theoretical Study on the Unexpected Catalytic Activity of Triethanolamine for the Carboxylative Cyclization of Propargylic Amines with CO2.
abstract: Chemical conversion of CO2under 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 CO2. 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 CO2to 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.
authors.affiliation: Collaborative Innovation Center of Henan Province for Green, Manufacturing of Fine Chemicals, School of Chemistry and Chemical, Engineering, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Normal University, Xinxiang, Henan, 453007, P. R. China.
authors.forename: Yuling
authors.initials: Y
authors.lastname: Zhao
authors.affiliation: Collaborative Innovation Center of Henan Province for Green, Manufacturing of Fine Chemicals, School of Chemistry and Chemical, Engineering, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Normal University, Xinxiang, Henan, 453007, P. R. China.
authors.forename: Jikuan
authors.initials: J
authors.lastname: Qiu
authors.affiliation: Collaborative Innovation Center of Henan Province for Green, Manufacturing of Fine Chemicals, School of Chemistry and Chemical, Engineering, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Normal University, Xinxiang, Henan, 453007, P. R. China.
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Li
authors.affiliation: Collaborative Innovation Center of Henan Province for Green, Manufacturing of Fine Chemicals, School of Chemistry and Chemical, Engineering, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Normal University, Xinxiang, Henan, 453007, P. R. China.
authors.forename: Huiyong
authors.initials: H
authors.lastname: Wang
authors.affiliation: Department of Chemical and Petroleum Engineering, University of Wyoming, Laramie, WY, 82071, USA.
authors.forename: Maohong
authors.initials: M
authors.lastname: Fan
authors.affiliation: Collaborative Innovation Center of Henan Province for Green, Manufacturing of Fine Chemicals, School of Chemistry and Chemical, Engineering, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Normal University, Xinxiang, Henan, 453007, P. R. China.
authors.forename: Jianji
authors.initials: J
authors.lastname: Wang
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002245:Carbon Dioxide / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004983:Ethanolamines / Q000737:chemistry*; D008962:Models, Theoretical; D023303:Oxazolidinones / Q000138:chemical synthesis; D059027:Recycling / Q000379:methods
chemical_list: D000480:Alkynes; D000588:Amines; D004983:Ethanolamines; D023303:Oxazolidinones; D002245:Carbon Dioxide; C009546:triethanolamine
keywords: CO2 conversion; alkanolamines; density functional calculations; heterocycles; organocatalysis