パラジウム触媒による酸素を用いた炭化水素類の末端選択的な酸化反応の開発を目指して

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  • Toward the Development of Palladium-catalyzed Terminal-selective Oxidations of Hydrocarbons Using Molecular Oxygen
  • パラジウム ショクバイ ニ ヨル サンソ オ モチイタ タンカスイソルイ ノ マッタン センタクテキ ナ サンカ ハンノウ ノ カイハツ オ メザシテ

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<p>Selective oxyfunctionalization at the terminal carbon of alkenes, alkanes and other hydrocarbons using molecular oxygen can become industrially and/or synthetically useful, environmental load-reducing synthetic methods for oxygen-containing organic compounds such as primary alcohols, aldehydes, and their derivatives. In this paper, we report the palladium-catalyzed synthesis of aldehydes and terminal acetals by anti-Markovnikov oxidation of vinylarenes using molecular oxygen (and also p-benzoquinone), and oxygenation of a benzyl ligand in palladium complexes. The former catalytic aerobic anti-Markovnikov oxidation reactions were efficiently promoted in the presence of a catalytic amount of electron-deficient cyclic alkenes such as maleimides and p-quinones, which would coordinate to palladium to accelerate the reaction as well as to stabilize in-situ formed Pd(0) species and suppress the deactivation. The latter oxygenation was remarkably accelerated by the addition of anion sources or Brønsted acids, affording oxygenated compounds such as benzaldehyde, benzyl hydroperoxide, and benzyl alcohol. The oxygenation with anion sources proceeds in a radical chain mechanism, while the oxygenation with Brønsted acids proceeds in a non-radical chain mechanism. Especially, the oxygenation with acids would be promising because catalytic oxygenation of toluenes and other hydrocarbons can be developed by combining the oxygenation step with a deprotonative C-H bond activation step.</p>

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