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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 17
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Original Articles

SiO2-NHC-CuI–Catalyzed N-Arylation of Imidazoles with Arylboronic Acids Under Base-Free Reaction Conditions

, &
Pages 2595-2605 | Received 04 Oct 2010, Published online: 29 May 2012
 

Abstract

N-Arylation of imidazoles with arylboronic acids was efficiently carried out in the presence of a catalytic amount of SiO2-NHC-CuI in methanol at room temperature under base-free reaction conditions. The reactions of a variety of arylboronic acids with imidazoles generated the corresponding products N-arylimidazoles in good to excellent yields. In addition, SiO2-NHC-CuI could be recovered and recycled for six consecutive trials without significant loss of its reactivity.

GRAPHICAL ABSTRACT

ACKNOWLEDGMENTS

We gratefully acknowledge financial support by the National Natural Science Foundation of China (20972057) and the Natural Science Foundation of Anhui (No. 090416223).

Notes

a SiO2-NHC-CuI(containing Cu 0.05 mmol, 5 mol%), imidazole (1.1 mmol), and phenylboronic acid (1.0 mmol) was carried out in solvent (3.0 mL) at 50 °C for 3 h under air.

b Isolated yields.

a SiO2-NHC-CuI(containing Cu 0.05 mmol, 5 mol%), azole (1.1 mmol), and arylboronic acid (1.0 mmol) was carried out in CH3OH (3.0 mL) at 50 °C for 3 h under air.

b Isolated yields.

a Reused SiO2-NHC-CuI (containing Cu 0.05 mmol, 5 mol%), imidazole (1.1 mmol), and phenylboronic acid (1.0 mmol) was carried out in CH3OH (3.0 mL) at 50 °C for 3 h under air.

b Isolated yields.

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