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Ni-Catalyzed cross coupling of aryl grignard reagents with aryl halides in a nonpolar solvent and an efficient synthesis of biaryls under neat conditions

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Abstract

This study details Ni-catalyzed cross coupling of aryl Grignard reagents with aryl halides in toluene, a nonpolar solvent with a high boiling point. The reaction was applied for the synthesis of various biaryls in good yields without the introduction of a large steric ligand. The Kumada-Tamao-Corriu(KTC) reaction in toluene was then successfully modified to proceed under neat conditions for the efficient syntheses of symmetrical biaryls, particularly in large-scale preparations. Unactivated aryl chlorides show higher reactivity than aryl bromides, particularly under neat conditions. Mechanistic investigations suggest a radical procedure for the catalytic cycle, and the origin of the radical intermediates being aryl halides.

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Authors and Affiliations

  1. State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, P. R. China

    Qiang Wu, Rizhe Jin, Chuanqing Kang, Wenhui Chen, Zheng Bian, Xiaoye Ma, Jinying Ding, Haiquan Guo, Xuepeng Qiu & Lianxun Gao

  2. University of Chinese Academy of Sciences, Beijing, 100864, P. R. China

    Qiang Wu

Authors
  1. Qiang Wu
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  2. Rizhe Jin
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  3. Chuanqing Kang
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  4. Wenhui Chen
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  5. Zheng Bian
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  6. Xiaoye Ma
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  7. Jinying Ding
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  8. Haiquan Guo
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  9. Xuepeng Qiu
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  10. Lianxun Gao
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Corresponding authors

Correspondence to Chuanqing Kang or Lianxun Gao.

Additional information

Supported by the National Basic Research Program of China(No.2014CB643603) and the Jilin Technology R&D Program, China(No.20140203003GX).

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Wu, Q., Jin, R., Kang, C. et al. Ni-Catalyzed cross coupling of aryl grignard reagents with aryl halides in a nonpolar solvent and an efficient synthesis of biaryls under neat conditions. Chem. Res. Chin. Univ. 32, 55–61 (2016). https://doi.org/10.1007/s40242-016-5261-0

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  • DOI: https://doi.org/10.1007/s40242-016-5261-0

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