Synthesis of a Ruthenium Porphyrin Having Substrate-Recognition Sites and Its Catalytic Regio-Selective Oxidation of Guests

DOI
  • Kito Akane
    Graduate School of Pharmaceutical Sciences, Nagoya City University
  • Shingaki Tomoteru
    Graduate School of Pharmaceutical Sciences, The University of Tokyo
  • Nagano Tetsuo
    Graduate School of Pharmaceutical Sciences, The University of Tokyo
  • Umezawa Naoki
    Graduate School of Pharmaceutical Sciences, Nagoya City University
  • Higuchi Tsunehiko
    Graduate School of Pharmaceutical Sciences, Nagoya City University

Bibliographic Information

Other Title
  • 基質認識能を有するポルフィリン金属錯体の合成と位置選択的アルカン酸化

Abstract

The selectivity on the oxidation by cytochrome P450 is probably due to appropriate arrangement of a substrate near the active intermediate of an enzyme by molecular recognition. We have found that ruthenium (Ru) porphyrin–pyridine N-oxide system is an exceptionally potent and efficient oxidizing one for unactivated alkanes, and so on. Ru porphyrin with substrate-recognition sites (1) is expected to be superior to simple Ru porphyrin in both selectivity and efficiency. 1H-NMR study showed that substrate 2 (tetradecane form), 3 (dodecane form) well makes 1:1 complex with 1 by multiple hydrogen bonding. By the addition of 2,6-dichloropyridine N-oxide, 2, 3 was oxidized with high regio-selectivity. On the other hand, Ru porphyrin without recognition sites gave no product. These results provide evidence that substrate recognition by a catalyst is advantageous for high regio-selectivity and high reactivity.

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Keywords

Details 詳細情報について

  • CRID
    1390001205634972032
  • NII Article ID
    130006997456
  • DOI
    10.14895/hannou.30.0.184.0
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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