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DMSO-catalyzed chlorination of alcohols using N-phenylbenzimidoyl chloride

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Abstract

N-phenylbenzimidoyl chloride has been demonstrated as an efficient chlorination reagent catalyzed by dimethyl sulfoxide (DMSO) in conversion of alcohols to corresponding chlorides. The reaction conditions were mild, and most of the substrates gave satisfactory yields. The configuration inversion of the chlorination was proved using optically active phenyl alcohols. The amount of DMSO can be as low as 0.001 eq without reducing the efficiency of the chlorination. A plausible mechanism for the reaction was proposed and proved by experiments. The reaction is stereoselective and potentially chemoselective among primary benzyl alcohols, secondary benzyl alcohols, and unactivated aliphatic alcohols.

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Acknowledgments

This work was supported by the Natural Science Research Program from Education Department of Hean Province (2011A150015), the Hean Polytechnic University Foundation for Doctor Teachers (B2010-65), and Hean Polytechnic University Foundation for the Youth (P051102).

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Authors and Affiliations

  1. Department of Chemistry, School of Physics-Chemistry, Henan Polytechnic University, Jiao Zuo, 454003, People’s Republic of China

    Qiang Wang & Zhou-Qing Xu

  2. Pharmaron Beijing Limited Co., 6 Taihe Road, BDA, Beijing, 100176, People’s Republic of China

    Jian Xu

  3. Junior Section of Tianjin Nankai Xiangyu School, Tianjin, 300100, People’s Republic of China

    Ji-Dan Yan

Authors
  1. Qiang Wang
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  2. Jian Xu
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  3. Zhou-Qing Xu
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  4. Ji-Dan Yan
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Correspondence to Qiang Wang.

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Wang, Q., Xu, J., Xu, ZQ. et al. DMSO-catalyzed chlorination of alcohols using N-phenylbenzimidoyl chloride. Res Chem Intermed 39, 2071–2076 (2013). https://doi.org/10.1007/s11164-012-0738-z

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  • DOI: https://doi.org/10.1007/s11164-012-0738-z

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