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A Biomimetic Catalytic Aerobic Functionalization of Phenols

Keywords:

  • ortho-Chinone;
  • Kupfer;
  • Oxidationen;
  • Synthesemethoden;
  • Tyrosinase

Abstract

The importance of aromatic C[BOND]O, C[BOND]N, and C[BOND]S bonds necessitates increasingly efficient strategies for their formation. Herein, we report a biomimetic approach that converts phenolic C[BOND]H bonds into C[BOND]O, C[BOND]N, and C[BOND]S bonds at the sole expense of reducing dioxygen (O2) to water (H2O). Our method hinges on a regio- and chemoselective copper-catalyzed aerobic oxygenation to provide ortho-quinones. ortho-Quinones are versatile intermediates, whose direct catalytic aerobic synthesis from phenols enables a mild and efficient means of synthesizing polyfunctional aromatic rings.

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