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Framework‐Copper‐Catalyzed C−N Cross‐Coupling of Arylboronic Acids with Imidazole: Convenient and Ligand‐Free Synthesis of N‐Arylimidazoles
Author(s) -
Devarajan Nainamalai,
Suresh Palaniswamy
Publication year - 2016
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201600480
Subject(s) - catalysis , ligand (biochemistry) , reagent , imidazole , chemistry , combinatorial chemistry , copper , substrate (aquarium) , heterogeneous catalysis , solvent , metal organic framework , coupling reaction , filtration (mathematics) , organic chemistry , polymer chemistry , biochemistry , oceanography , receptor , statistics , mathematics , adsorption , geology
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.