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Green Conversion of CO<sub>2</sub> and Propargylamines Triggered by Triply Synergistic Catalytic Effects in Metal–Organic Frameworks

Xiao‐Lei Jiang, Yue‐E Jiao, Sheng‐Li Hou, Liang‐Chen Geng, Hao‐Zhe Wang, Bin Zhao

2021Angewandte Chemie International Edition148 citationsDOI

Abstract

Abstract Cyclization of propargylamines with CO 2 to obtain 2‐oxazolidone heterocyclic compounds is an essential reaction in industry but it is usually catalyzed by noble‐metal catalysts with organic bases as co‐catalysts under harsh conditions. We have synthesized a unique Cu I /Cu II mixed valence copper‐based framework {[(Cu I 6 I 5 )Cu 3 II L 6 (DMA) 3 ](NO 3 )⋅9DMA} n ( 1 ) with good solvent and thermal stability, as well as a high density of uncoordinated amino groups evenly distributed in the large nanoscopic channels. Catalytic experiments show that 1 can effectively catalyze the reaction of propargylamines with CO 2 , and the yield can reach 99 %. The turnover frequency (TOF) reaches a record value of 230 h −1 , which is much higher than that of reported noble‐metal catalysts. Importantly, this is the first report of heterogeneously catalyzed green conversion of propargylamines with CO 2 without solvents and co‐catalysts under low temperature and atmospheric pressure. A mechanistic study reveals that a triply synergistic catalytic effect between Cu I /Cu II and uncoordinated amino groups promotes highly efficient and green conversion of CO 2 . Furthermore, 1 directly catalyzes this reaction with high efficiency when using simulated flue gas as a CO 2 source.

Topics & Concepts

CatalysisChemistryNoble metalCopperYield (engineering)Valence (chemistry)MetalSolventAtmospheric pressureNanoscopic scaleMetal-organic frameworkCombinatorial chemistryInorganic chemistryAdsorptionMaterials scienceOrganic chemistryNanotechnologyMetallurgyOceanographyGeologyCarbon dioxide utilization in catalysisCO2 Reduction Techniques and CatalystsAsymmetric Hydrogenation and Catalysis