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Ag I /TMG‐Promoted Cascade Reaction of Propargyl Alcohols, Carbon Dioxide, and 2‐Aminoethanols to 2‐Oxazolidinones
Author(s) -
Li XueDong,
Song QingWen,
Lang XianDong,
Chang Yao,
He LiangNian
Publication year - 2017
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201700297
Subject(s) - chemistry , propargyl , propargyl alcohol , alcohol , medicinal chemistry , cascade reaction , organic chemistry , catalysis , combinatorial chemistry
Chemical valorization of CO 2 to access various value‐added compounds has been a long‐term and challenging objective from the viewpoint of sustainable chemistry. Herein, a one‐pot three‐component reaction of terminal propargyl alcohols, CO 2 , and 2‐aminoethanols was developed for the synthesis of 2‐oxazolidinones and an equal amount of α‐hydroxyl ketones promoted by Ag 2 O/TMG (1,1,3,3‐tetramethylguanidine) with a TON (turnover number) of up to 1260. By addition of terminal propargyl alcohol, the thermodynamic disadvantage of the conventional 2‐aminoethanol/CO 2 coupling was ameliorated. Mechanistic investigations including control experiments, DFT calculation, kinetic and NMR studies suggest that the reaction proceeds through a cascade pathway and TMG could activate propargyl alcohol and 2‐aminoethanol through the formation of hydrogen bonds and also activate CO 2 .