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The first copper-catalyzed N-arylation of 2-imidazolines is described. The reaction affords compounds with desirable lead-like characteristics in high yield with practical simplicity under inexpensive, "ligand-free" conditions. The cross coupling was successful with electron-rich and electron-poor aromatic iodides. Substrates bearing halides, esters, nitriles, and free hydroxyls are well tolerated, providing reactive handles for further functionalization, as are pyridines. In addition, the regioselective N-arylation of a 4-substituted imidazoline is reported.


Owen A Davis, Matthew Hughes, James A Bull. Copper-catalyzed N-arylation of 2-imidazolines with aryl iodides. The Journal of organic chemistry. 2013 Apr 5;78(7):3470-5

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PMID: 23464665

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