Palladium Nanoparticle-Catalyzed Direct Ethynylation of Aliphatic Carboxylic Acid Derivatives via C(sp3)[BOND]H Bond Functionalization

Authors

  • Mohammad Al-Amin,

    1. Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan
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  • Mitsuhiro Arisawa,

    Corresponding author
    1. Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan
    2. Present address: Graduate School of Pharmaceutical Sciences, Osaka University, 1–6 Yamada-oka, Suita, Osaka 565-0871, Japan
    • Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan===

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  • Satoshi Shuto,

    1. Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan
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  • Yusuke Ano,

    1. Department of Applied Chemistry, Faculty of Engineering, Osaka University, 2–1 Yamada-oka, Suita, Osaka 565-0871, Japan
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  • Mamoru Tobisu,

    1. Department of Applied Chemistry, Faculty of Engineering, Osaka University, 2–1 Yamada-oka, Suita, Osaka 565-0871, Japan
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  • Naoto Chatani

    1. Department of Applied Chemistry, Faculty of Engineering, Osaka University, 2–1 Yamada-oka, Suita, Osaka 565-0871, Japan
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Abstract

We have developed a sulfur-modified, gold-supported palladium material (SAuPd) with palladium, Pd, nanoparticles on its surface; it is a recyclable, low-leaching Pd catalyst. Here we report, using SAuPd, the first example of Pd nanoparticle-catalyzed, unactivated C(sp3)[BOND]H bond functionalization of amides, using 8-aminoquinoline as a directing group, to yield ethynylated products. The low leaching properties of SAuPd enabled it to be recycled and reused 10 times for C(sp3)[BOND]H bond functionalization.

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