Nanopalladium on Amino-Functionalized Mesocellular Foam as an Efficient and Recyclable Catalyst for the Selective Transfer Hydrogenation of Nitroarenes to Anilines

Authors

  • Oscar Verho,

    1. Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm (Sweden)
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  • Anuja Nagendiran,

    1. Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm (Sweden)
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  • Dr. Cheuk-Wai Tai,

    1. Department of Materials and Environmental Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91 Stockholm (Sweden)
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  • Dr. Eric V. Johnston,

    Corresponding author
    1. Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm (Sweden)
    • Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm (Sweden)

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  • Prof. Dr. Jan-E. Bäckvall

    Corresponding author
    1. Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm (Sweden)
    • Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91, Stockholm (Sweden)

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Abstract

Herein, we report on the use of nanopalladium on amino-functionalized siliceous mesocellular foam as an efficient heterogeneous catalyst for the transfer hydrogenation of nitroarenes to anilines. In all cases, the protocol proved to be highly selective and favored the formation of the desired aniline as the single product in high yields with short reaction times if naturally occurring and renewable γ-terpinene was employed as the hydrogen donor. Furthermore, the catalyst displayed excellent recyclability over five cycles and negligible leaching of metal into solution, which makes it an eco-friendly and economic catalyst to perform this transformation. The scalability of the protocol was demonstrated with the reduction of 4-nitroanisole on a 2 g scale, in which p-anisidine was isolated in 98 % yield.

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