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Palladium-catalyzed regioselective synthesis of 2(2\(^{\prime }\)-biphenyl)benzimidazoles through C–H activation

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Abstract

An efficient palladium-catalyzed strategy through C–H bond activation for the synthesis of 2(2\(^{\prime }\)-biphenyl)-benzimidazoles is reported herein. The regioselective C–C bond formation proceeds in a sealed tube via oxidative C–H activation of ortho-directed 2-aryl-benzimidazole to couple with various iodobenzene analogs in high yields. This arylation exhibited high regioselectivity which is able to increase molecular diversity in difficult functionalized positions of parent molecules. This strategy provides a convenient and simple synthesis of biphenyl heterocyclic compounds with high regioselectivity.

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Acknowledgments

The authors wish to thank the National Science Council of Taiwan for financial support and the authorities of the National Chiao Tung University for providing the laboratory facilities. This study was particularly supported by the “Centre for Bioinformatics Research of Aiming for the Top University Plan” of the National Chiao Tung University and Ministry of Education, Taiwan.

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  1. Laboratory of Combinatorial Drug Design, Department of Applied Chemistry, National Chiao Tung University, Hsin-chu, 300-10, Taiwan

    Li-Hsun Chen, Tz-Yi Wu, Vijaykumar Paike & Chung-Ming Sun

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  1. Li-Hsun Chen
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Correspondence to Chung-Ming Sun.

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Chen, LH., Wu, TY., Paike, V. et al. Palladium-catalyzed regioselective synthesis of 2(2\(^{\prime }\)-biphenyl)benzimidazoles through C–H activation. Mol Divers 17, 641–649 (2013). https://doi.org/10.1007/s11030-013-9460-z

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