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Cu-Mediated Direct Aryl C[BOND]H Halogenation: a Strategy to Control Mono- and Di-Selectivity

Authors

  • Zhi-Jun Du,

    1. Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun, Jilin 130022 (P.R. China), Fax: (+86) 0431-85262926
    2. The University of Chinese Academy of Sciences, Beijing 100864 (P.R. China)
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  • Prof. Lian-Xun Gao,

    1. Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun, Jilin 130022 (P.R. China), Fax: (+86) 0431-85262926
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  • Prof. Ying-Jie Lin,

    1. Department of Chemistry, Jilin University, Changchun, Jilin 130012 (P.R. China)
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  • Prof. Fu-She Han

    Corresponding author
    1. Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun, Jilin 130022 (P.R. China), Fax: (+86) 0431-85262926
    • Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun, Jilin 130022 (P.R. China), Fax: (+86) 0431-85262926

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Abstract

A protocol for the copper-mediated direct aryl C[BOND]H halogenation is presented. Highly selective mono- and di-halogenations are achieved by using acyl hypohalites, generated in situ from the readily available carboxylic acid and N-halosuccinimides (NXS; X=Br and Cl) as powerful halogenating reagents. The correct choice of carboxylic acid additives and solvents is essential for both high yield and selectivity. Consequently, the use of inexpensive Cu catalyst and the new strategy for the in situ generation of acyl hypohalite halogenating reagents from the readily affordable and easily-to-handle carboxylic acid and NXS (X=Br and Cl) offers advantages for practical application.

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