Framework‐Copper‐Catalyzed C−N Cross‐Coupling of Arylboronic Acids with Imidazole: Convenient and Ligand‐Free Synthesis of N‐Arylimidazoles. Issue 18 (16th August 2016)

• Record Type: Journal Article
• Authors: Devarajan, Nainamalai; Suresh, Palaniswamy
• Is Part Of: ChemCatChem. Volume 8:Issue 18(2016)
• Page Start: 2953
• Page End: 2960
• Publication Date: 2016-08-16
• Subjects: cross-coupling -- copper -- heterogeneous catalysis -- metal–organic frameworks -- nitrogen heterocycles; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201600480
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: A convenient and environmentally benign synthesis of N‐arylimidazoles has been demonstrated by a straightforward reaction catalyzed by the unsaturated coordination sites of Cu in the copper terephthalate metal–organic framework (Cu(tpa)‐MOF). A series of N‐arylimidazoles has been synthesized in excellent yields by the C−N cross‐coupling reaction of arylboronic acids and imidazoles catalyzed by the Cu(tpa)‐MOF using ethanol as a benign solvent. The present ligand‐free catalytic system proceeds smoothly under mild conditions, avoids stoichiometric Cu reagents, tolerates many functional groups, has a wide substrate scope, and is feasible with other nitrogen heterocycles. The stability and heterogeneity of the catalyst is evidenced by the results of a heterogeneity test, and the catalyst can be reused several times without a loss of activity. The easy preparation of the catalyst, its stability, recovery by simple filtration, and reusability reveal Cu(tpa) MOF as a versatile catalyst for academic and industrial applications. Abstract : Coupling in frameworks : The copper terephthalate metal–organic framework (Cu(tpa)‐MOF) is an efficient, reusable, and benign heterogeneous catalyst for the C−N cross‐coupling of arylboronic acids with imidazoles. A series of N‐arylimidazoles is synthesized in excellent yields catalyzed by the unsaturated coordination sites of Cu in the Cu(tpa)‐MOF. The easy preparation of the catalyst, its stability, recovery by simple filtration, and reusability reveal Cu(tpa)‐MOF as a versatile catalyst for diverse applications.