Selective Activation of Alcohols in the Presence of Reactive Amines over Intermetallic PdZn: Efficient Catalysis for Alcohol-Based <i>N</i>-Alkylation of Various Amines

DOI Web Site 被引用文献12件 参考文献43件
  • Shinya Furukawa
    Department of Chemistry, School of Science, Tokyo Institute of Technology, 2-12-1-E1-10 Ookayama, Meguro-ku, Tokyo 152-8551, Japan
  • Ryohei Suzuki
    Department of Chemistry, School of Science, Tokyo Institute of Technology, 2-12-1-E1-10 Ookayama, Meguro-ku, Tokyo 152-8551, Japan
  • Takayuki Komatsu
    Department of Chemistry, School of Science, Tokyo Institute of Technology, 2-12-1-E1-10 Ookayama, Meguro-ku, Tokyo 152-8551, Japan

書誌事項

公開日
2016-08-09
資源種別
journal article
DOI
  • 10.1021/acscatal.6b01677
公開者
American Chemical Society (ACS)

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説明

Pd-based intermetallic compounds supported on Al2O3 (PdxMy/Al2O3, where M = Bi, Cu, Fe, Ga, In, Pb, Sn, or Zn) were prepared and tested as catalysts for the selective activation of alcohols in the presence of reactive amines, which is highly challenging and is the key strategy for alcohol-based N-alkylation of amines. Although the Pd/Al2O3 catalyst exhibited a high catalytic activity, undesired side reactions such as amine dimerization (via amine activation) and C–O bond scission occurred, resulting in a poor yield of the N-alkylation product. In contrast, the PdZn/Al2O3 catalyst acted as an efficient catalyst for this reaction, displaying high catalytic activities, selectivities, and atom efficiencies and a wide substrate scope. Detailed kinetic and computational studies revealed that the relative affinity of Pd for alcohol and amine drastically changes by the formation of a PdZn intermetallic phase. On monometallic Pd, the adsorption and activation of amines are preferred over those of alcohols in terms...

収録刊行物

  • ACS Catalysis

    ACS Catalysis 6 (9), 5946-5953, 2016-08-09

    American Chemical Society (ACS)

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