Intermolecular Olefin Cross-Metathesis Initiated by the Umpolung of Enol Ethers

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  • エノールエーテルの極性転換によって開始される分子間オレフィンクロスメタセシス
  • エノールエーテル ノ ゴクセイ テンカン ニ ヨッテ カイシ サレル ブンシ カン オレフィンクロスメタセシス

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Abstract

Electrochemical approaches have proven to be effective for regulating either one or two electron transfers at the surface of the electrodes that afford not only various functional group transformations, but also a wide variety of carbon-carbon bond forming reactions. Especially, the anodic oxidation of electron-rich olefins generates their radical cations, which are then trapped by a variety of nucleophiles, leading to a number of interesting cyclizations. These anodic transformations are initiated by the umpolung processes that normally nucleophilic electron-rich olefins are anodically oxidized to give electrophilic radical cations to react with second nucleophiles. Meanwhile, unactivated olefins have been found to act as carbon nucleophiles in lithium perchlorate/nitromethane electrolyte solutions that can be used to construct intermolecular carbon-carbon bonds. The use of enol ethers as electron-rich olefins has led to the formation of cyclobutane-like intermediates through which intermolecular olefin cross-coupling and -metathesis are achieved.

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