Amidation via ligand-free direct oxidative C(sp3)-H/NH coupling with Cu-CPO-27 metal-organic framework as a recyclable heterogeneous catalyst

作者: Thanh T. Hoang , Hanh T.H. Nguyen , Tien T. Le , Dung T. Le , Thanh Truong

DOI: 10.1016/J.TET.2016.10.059

关键词: LigandOxidative phosphorylationMetal-organic frameworkOrganic chemistryPolymer chemistryDABCOChemistryCopperCatalysisCoupling (electronics)Heterogeneous catalysis

摘要: Abstract A copper-based metal-organic framework Cu-CPO-27 was synthesized, and used as a recyclable catalyst for the amidation of unactivated alkanes by benzamides via direct oxidative C(sp3)-H/N H coupling under ligand-free conditions. Using catalytic amount transformation, high yields N-cyclohexyl were achieved. The more catalytically active than other Cu-MOFs such Cu3(BTC)2, Cu(BDC), Cu(EDB), Cu2(BPDC)2(BPY), Cu2(BDC)2(DABCO), Cu2(EDB)2(BPY). also exhibited advantages compared to several salts, including Cu(OAc)2, CuCl2, CuBr, CuI, CuCl, Cu(NO3)2, CuSO4. could be reused times transformation while its activity not decreased significantly. To best our knowledge, previously performed heterogeneous catalysis

参考文章(82)
Vittorio Pace, Pilar Hoyos, María Fernández, José V. Sinisterra, Andrés R. Alcántara, 2-Methyltetrahydrofuran as a suitable green solvent for phthalimide functionalization promoted by supported KF Green Chemistry. ,vol. 12, pp. 1380- 1382 ,(2010) , 10.1039/C0GC00113A
Michael Ghobrial, Michael Schnürch, Marko D. Mihovilovic, Direct Functionalization of (Un)protected Tetrahydroisoquinoline and Isochroman under Iron and Copper Catalysis: Two Metals, Two Mechanisms Journal of Organic Chemistry. ,vol. 76, pp. 8781- 8793 ,(2011) , 10.1021/JO201511D
Weijia Xie, Jie Yang, Baiquan Wang, Bin Li, Regioselective Ortho Olefination of Aryl Sulfonamide via Rhodium-Catalyzed Direct C–H Bond Activation Journal of Organic Chemistry. ,vol. 79, pp. 8278- 8287 ,(2014) , 10.1021/JO5015239
Eric Valeur, Mark Bradley, Amide Bond Formation: Beyond the Myth of Coupling Reagents Chemical Society Reviews. ,vol. 38, pp. 606- 631 ,(2009) , 10.1039/B701677H
Shilpa A. Worlikar, Richard C. Larock, Palladium-Catalyzed One-Step Synthesis of Isoindole-1,3-diones by Carbonylative Cyclization of o-Halobenzoates and Primary Amines Journal of Organic Chemistry. ,vol. 73, pp. 7175- 7180 ,(2008) , 10.1021/JO800936H
Shu-Lan Zhu, Sha Ou, Min Zhao, Hong Shen, Chuan-De Wu, A porous metal–organic framework containing multiple active Cu2+ sites for highly efficient cross dehydrogenative coupling reaction Dalton Transactions. ,vol. 44, pp. 2038- 2041 ,(2015) , 10.1039/C4DT03371J
Giao H. Dang, Thanh D. Nguyen, Dung T. Le, Thanh Truong, Nam T. S. Phan, Direct Oxidative Amidation between N,N-dimethylanilines and Anhydrides Using Metal-Organic Framework [Cu2(EDB)2(BPY)] as an Efficient Heterogeneous Catalyst† ChemPlusChem. ,vol. 79, pp. 1129- 1137 ,(2014) , 10.1002/CPLU.201402090