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Synthesis of Chiral Imidazolium Salts from a Carbohydrate and Their Application in Pd-Catalyzed Suzuki–Miyaura Reaction

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Abstract

A series of chiral 1-(acetylated glucopyranosyl)-3-substituted-imidazolium salts [3-substitute = n-butyl (1a), 3-bromopropyl (1b), 2-chloromethyl benzyl (1c), and 4-chloromethyl benzyl (1d)] have been synthesized. Preliminary catalytic studies show that these imidazolinium salts are remarkably efficient in Pd-catalyzed Suzuki–Miyaura reaction. Functionalized aryl boronic acids reaction with aryl halides (including aryl iodides, aryl bromides and activated aryl chlorides) using environmentally friendly conditions (ethanol aqueous and ambient). The excellent isolate yields reveal that the bulky carbohydrate unit is promising for the construction of highly active transition-metal catalyst.

Graphical Abstract

Four C-1 bonded sugar-containing chiral imidazolium salts 1a–d were synthesized and they all exhibited excellent catalytic activity in Pd-catalyzed Suzuki reactions. Pd/1a is most effective for the coupling of functionalized arylboronic acids with arylhalides including activated arylchlorides in ethanol aqueous under air.

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Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (No. 21241005, 21363001, 2146002 and 21061001), the Key Laboratory of Jiangxi University for Functional Materials Chemistry, and Fujian Normal University.

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Gannan Normal University, Ganzhou, 341000, People’s Republic of China

    Zhonggao Zhou, Jiabin Qiu, Lifang Xie, Fan Du, Guohai Xu & Yongrong Xie

  2. College of Materials Science and Engineering, Fujian Normal University, Fuzhou, 350007, People’s Republic of China

    Zhonggao Zhou & Qidan Ling

  3. Fujian Key Laboratory of Polymer Materials, Fuzhou, 350007, People’s Republic of China

    Qidan Ling

Authors
  1. Zhonggao Zhou
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  2. Jiabin Qiu
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  3. Lifang Xie
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  4. Fan Du
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  5. Guohai Xu
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  6. Yongrong Xie
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  7. Qidan Ling
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Corresponding authors

Correspondence to Yongrong Xie or Qidan Ling.

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Zhou, Z., Qiu, J., Xie, L. et al. Synthesis of Chiral Imidazolium Salts from a Carbohydrate and Their Application in Pd-Catalyzed Suzuki–Miyaura Reaction. Catal Lett 144, 1911–1918 (2014). https://doi.org/10.1007/s10562-014-1323-4

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  • DOI: https://doi.org/10.1007/s10562-014-1323-4

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