Feeding the Heck Reaction with Alcohol: One-Pot Synthesis of Stilbenes from Aryl Alcohols and Bromides

Authors

  • Paul Colbon,

    1. Liverpool Centre for Materials & Catalysis, Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, U.K. Fax: (+44)-151-794-3588 (homepage:http://pcwww.liv.ac.uk/~jxiao)
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  • Jonathan H. Barnard,

    1. Liverpool Centre for Materials & Catalysis, Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, U.K. Fax: (+44)-151-794-3588 (homepage:http://pcwww.liv.ac.uk/~jxiao)
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  • Mark Purdie,

    1. PR&D, Global Research & Development, AstraZeneca, Silk Road Business Park, Macclesfield, SK10 2NA, U.K.
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  • Keith Mulholland,

    1. PR&D, Global Research & Development, AstraZeneca, Silk Road Business Park, Macclesfield, SK10 2NA, U.K.
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  • Ivan Kozhevnikov,

    1. Liverpool Centre for Materials & Catalysis, Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, U.K. Fax: (+44)-151-794-3588 (homepage:http://pcwww.liv.ac.uk/~jxiao)
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  • Jianliang Xiao

    Corresponding author
    1. Liverpool Centre for Materials & Catalysis, Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, U.K. Fax: (+44)-151-794-3588 (homepage:http://pcwww.liv.ac.uk/~jxiao)
    • Liverpool Centre for Materials & Catalysis, Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, U.K. Fax: (+44)-151-794-3588
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Abstract

Aryl alcohols are employed as feedstock for the Heck reaction. Keggin-type heteropolyacids catalyse the selective dehydration of the alcohols to styrenes, which, in one-pot, undergo palladium-catalysed Heck arylation with aryl bromides, affording broadly functionalised stilbenes. The choice of solvent is critical for the cascade dehydration–Heck reaction, with electron-rich aryl alcohols preferring a basic medium while electron-deficient ones demanding solvents of lower basicity.

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