Synthesis of Acrylonitriles through an FeCl3-Catalyzed Domino Propargylic Substitution/Aza-Meyer–Schuster Rearrangement Sequence

Authors

  • Lu Hao,

    1. Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian (P.R. China), Fax: (+86) 592-2180318
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  • Feng Wu,

    1. School of Pharmaceutical Sciences, Xiamen University, Xiamen 361005, Fujian (P.R. China), Fax: (+86) 592-2180318
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  • Zong-Cang Ding,

    1. Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian (P.R. China), Fax: (+86) 592-2180318
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  • Su-Xia Xu,

    1. Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian (P.R. China), Fax: (+86) 592-2180318
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  • Yan-Li Ma,

    1. Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian (P.R. China), Fax: (+86) 592-2180318
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  • Prof. Dr. Li Chen,

    1. Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian (P.R. China), Fax: (+86) 592-2180318
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  • Prof. Dr. Zhuang-Ping Zhan

    Corresponding author
    1. Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian (P.R. China), Fax: (+86) 592-2180318
    2. School of Pharmaceutical Sciences, Xiamen University, Xiamen 361005, Fujian (P.R. China), Fax: (+86) 592-2180318
    • Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian (P.R. China), Fax: (+86) 592-2180318
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Abstract

original image

Nontoxic cyanide source: An unprecedented route to acrylonitriles by employing propargylic alcohols and para-tolylsulfonohydrazide as a combined cyano source has been developed (see scheme). This efficient and practical cyanation reaction proceeds through an FeCl3-catalyzed domino propargylic substitution/aza-Meyer–Schuster rearrangement sequence, the rearrangement process of which is reported for the first time.

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