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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2009 - Issue 2
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Original Articles

2,2′-Biimidazole as an Efficient Ligand for Copper(I)-Catalyzed C‒N Coupling Reactions

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Pages 222-228 | Received 28 May 2008, Published online: 29 Dec 2009
 

Abstract

An efficient copper(I)-catalyzed system using 2,2′-biimidazole as the ligand was applied to N-arylation of a broad spectrum of nitrogen nucleophiles with aryl halides. The reactions were carried out in relatively mild conditions with good to excellent yields.

ACKNOWLEDGMENTS

We thank the National Natural Science Foundation of China (Nos. 30772652 and 90813026) and Major Projects the National Science and Technology “Creation of major new drugs” (No. 2009ZX09501-010).

Notes

a Reaction conditions: iodobenzene (1.0 equiv), benzylamine (1.2 equiv), CuI (10 mol%), ligand (20 mol%), Cs2CO3 (2 equiv), under N2 atmosphere at 100°C for 24 h.

b Isolated yield.

c DMF:H2O (1:1) as solvent.

a Reaction conditions: aryl halide (1.0 equiv), N-containing compound (1.5 equiv), CuI (10 mol%), A (20 mol%), and Cs2CO3 (2.0 equiv).

b Isolated yield.

c 20 equiv of amine was used to avoid the low yield due to its low boiling point.

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