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Binuclear Tridentate Hemilabile Copper(I) Catalysts for Utilization of CO2into Oxazolidinones from Propargylic Amines

Authors :
Chen, Fei
Tao, Sheng
Deng, Qian-Qian
Wei, Donghui
Liu, Ning
Dai, Bin
Source :
The Journal of Organic Chemistry; December 2020, Vol. 85 Issue: 23 p15197-15212, 16p
Publication Year :
2020

Abstract

Four binuclear tridentate copper(I) complexes were synthesized based on the trans effect of the hybrid ligands. The catalytic performance and behavior of the prepared copper(I) complexes were evaluated in the carboxylative cyclization of propargylic amines with CO2. The combined use of copper(I) complexes and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) provided a catalytic system for the synthesis of a wide range of oxazolidinones from various propargylic amines and CO2under mild reaction conditions (room temperature—40 °C and 1 bar CO2). The key factor for the success of the protocol is the use of copper complexes possessing the quality of hemilabile properties between N-heterocyclic carbenes and nitrogen donors. NMR measurements, density functional theory (DFT) calculations, and previous reports for the coordination behavior of the nickel complexes support the existence of the trans effect between N-heterocyclic carbenes and nitrogen donors.

Details

Language :
English
ISSN :
00223263
Volume :
85
Issue :
23
Database :
Supplemental Index
Journal :
The Journal of Organic Chemistry
Publication Type :
Periodical
Accession number :
ejs54589584
Full Text :
https://doi.org/10.1021/acs.joc.0c02065