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Palladium-Catalyzed Heck-Type Reactions of Allylic Esters with Arylboronic Acids or Potassium Aryltrifluoroborates

Authors

  • Bo Yao,

    1. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, People's Republic of China, Fax: (+86)-577-8668-9372; phone: (+86)-577-8668-9615
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  • Yan Liu,

    1. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, People's Republic of China, Fax: (+86)-577-8668-9372; phone: (+86)-577-8668-9615
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  • Meng-Ke Wang,

    1. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, People's Republic of China, Fax: (+86)-577-8668-9372; phone: (+86)-577-8668-9615
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  • Jin-Heng Li,

    Corresponding author
    1. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, People's Republic of China, Fax: (+86)-731-8887-2531; phone: (+86)-731-8887-2576
    • State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, People's Republic of China, Fax: (+86)-731-8887-2531; phone: (+86)-731-8887-2576
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  • Ri-Yuan Tang,

    1. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, People's Republic of China, Fax: (+86)-577-8668-9372; phone: (+86)-577-8668-9615
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  • Xing-Guo Zhang,

    1. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, People's Republic of China, Fax: (+86)-577-8668-9372; phone: (+86)-577-8668-9615
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  • Chen-Liang Deng

    Corresponding author
    1. College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, People's Republic of China, Fax: (+86)-577-8668-9372; phone: (+86)-577-8668-9615
    • College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, People's Republic of China, Fax: (+86)-577-8668-9372; phone: (+86)-577-8668-9615
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Abstract

A selective and general route to (E)-1,3-diaryl-prop-1-enes and (E)-3-arylallyl acetates has been developed by palladium-catalyzed Heck-type reactions of allylic esters with arylboronic acids or potassium aryltrifluoroborates. The present method selectively proceeds including β-OAc elimination or β-H elimination on the basis of the boronic acids. Whereas a variety of allylic esters were reacted with arylboronic acids, palladium(II) acetate [Pd(OAc)2], tetra(n-butyl)ammonium chloride [(n-Bu)4NCl] and postassium dihydrogen phosphate (KH2PO4) to afford the corresponding diarylation products in moderate to good yields, treatment of allylic esters with potassium aryltrifluoroborates furnished the corresponding monoarylation products.

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