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Molecules 2012, 17(11), 12506-12520; doi:10.3390/molecules171112506
Article

Aqueous Synthesis of 1-H-2-Substituted Benzimidazoles via Transition-Metal-Free Intramolecular Amination of Aryl Iodides

1,2, 1, 1,2,* , 1 and 1,*
Received: 25 September 2012; in revised form: 17 October 2012 / Accepted: 21 October 2012 / Published: 24 October 2012
(This article belongs to the Section Organic Synthesis)
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Abstract: A straightforward method has been developed for the synthesis of the benzimidazole ring system through a carbon-nitrogen cross-coupling reaction. In the presence of 2.0 equiv. of K2CO3 in water at 100 °C for 30 h, the intramolecular cyclization of N-(2-iodoaryl)benzamidine provides benzimidazole derivatives in moderate to high yields. Remarkably, the procedure occurs exclusively in water and doesn’t require the use of any additional reagent/catalyst, rendering the methodology highly valuable from both environmental and economical points of view.
Keywords: benzimidazoles; aqueous synthesis; N-arylation; transition-metal-free conditions; aryl iodides benzimidazoles; aqueous synthesis; N-arylation; transition-metal-free conditions; aryl iodides
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Chen, C.; Chen, C.; Li, B.; Tao, J.; Peng, J. Aqueous Synthesis of 1-H-2-Substituted Benzimidazoles via Transition-Metal-Free Intramolecular Amination of Aryl Iodides. Molecules 2012, 17, 12506-12520.

AMA Style

Chen C, Chen C, Li B, Tao J, Peng J. Aqueous Synthesis of 1-H-2-Substituted Benzimidazoles via Transition-Metal-Free Intramolecular Amination of Aryl Iodides. Molecules. 2012; 17(11):12506-12520.

Chicago/Turabian Style

Chen, Chunxia; Chen, Chen; Li, Bin; Tao, Jingwei; Peng, Jinsong. 2012. "Aqueous Synthesis of 1-H-2-Substituted Benzimidazoles via Transition-Metal-Free Intramolecular Amination of Aryl Iodides." Molecules 17, no. 11: 12506-12520.


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