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Palladium-Catalyzed Direct C[BOND]H Arylation of Enamides with Simple Arenes

Authors

  • Dr. Sreekumar Pankajakshan,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)
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  • Dr. Yun-He Xu,

    1. Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P. R. China)
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  • Jun Kee Cheng,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)
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  • Man Ting Low,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)
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  • Prof. Dr. Teck-Peng Loh

    Corresponding author
    1. Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P. R. China)
    2. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)
    • Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P. R. China)
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  • We gratefully acknowledge Nanyang Technological University and the Singapore Ministry of Education Academic Research Fund (MOE2011-T2-1-013) for the funding support for this research. We thank Prof. S. Chiba for the helpful discussions.

Abstract

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Z only: An atom-economical synthetic route towards arylated Z-enamides through double C[BOND]H functionalization is described. The Z/E selectivity of the palladium-catalyzed monoarylation is absolute (step A in scheme), and the molecular complexity of the products can be further endowed by a sequential second arylation, which requires the use of trifluoracetic acid (TFA; step B).

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