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

doi:10.3390/molecules171112506

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

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

Chunxia Chen^1,2, Chen Chen¹, Bin Li^1,2,* , Jingwei Tao¹ and Jinsong Peng^1,*

¹ Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040, China ² Post-Doctoral Mobile Research Station of Forestry Engineering, Northeast Forestry University, Harbin 150040, China

* Authors to whom correspondence should be addressed.

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

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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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