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Carbon–Carbon Bond Formation: Palladium-Catalyzed Oxidative Cross-Coupling of N-Tosylhydrazones with Allylic Alcohols

Authors

  • Huoji Chen,

    1. School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (P.R. China), Fax: (+86) 20-8711-2906
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  • Li Huang,

    1. School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (P.R. China), Fax: (+86) 20-8711-2906
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  • Wei Fu,

    1. School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (P.R. China), Fax: (+86) 20-8711-2906
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  • Xiaohang Liu,

    1. School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (P.R. China), Fax: (+86) 20-8711-2906
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  • Prof. Dr. Huanfeng Jiang

    Corresponding author
    1. School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (P.R. China), Fax: (+86) 20-8711-2906
    • School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (P.R. China), Fax: (+86) 20-8711-2906
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Abstract

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In the zone: Pd-catalyzed oxidative cross-coupling of N-tosylhydrazones with allylic alcohols leads to C[BOND]C bond formation. A palladium–carbene migratory insertion is proposed to play the key role in this transformation. The reaction proceeds with readily available starting materials to afford substituted alkenes in a highly stereoselective manner (see scheme).

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