Facile CuI-Catalyzed Arylation of Azoles and Amides Using Simple Enaminones as Efficient Ligands

Abstract

(E)-3-(Dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one was found to be an excellent ligand for copper-catalyzed N-arylation of azoles and amides with aryl halides under mild conditions. The reaction took place at 82 ˚C in MeCN with broad functional-group compatibility. A combination of the ligand and CuI proved to be an efficient catalytic system to promote the coupling reactions of aryl halides with azoles and amides.

copper - ligand - azoles - amides - arylation

References and Notes

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General Procedure
All chemicals were obtained from commercial source and used without further purification. A stirred suspension of aryl halides (0.5 mmol), azoles or amides (0.5 mmol), CuI powder (0.05 mmol), Cs₂CO₃ (1.0 mmol), and L5 (0.1 mmol) in MeCN was refluxed for 12 h (monitored by TLC) under nitrogen. After the mixture was cooled to r.t., the MeCN was removed in vacuo. The solid was then extracted with EtOAc (3 × 10 mL), washed with H₂O (3 × 10 mL), and dried over Na₂SO₄. After the solvent was removed, the crude mixture was purified by silica gel column chromatography to provide the desired product.