New Route to 2,5-Disubstituted Furans

  • Author: ChemViews
  • Published Date: 22 July 2011
  • Source / Publisher: European Journal of Organic Chemistry/Wiley-VCH
  • Copyright: WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: New Route to 2,5-Disubstituted Furans

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2-Substituted and 2,5-disubstituted furans are important substructures of several drugs currently in clinical use.

Bernd Schmidt and Diana Geißler, Universität Potsdam, Golm, Germany, have established a one-flask method for the synthesis of furans, ultimately starting from simple diallyl ethers. The sequence consists of transition-metal-catalyzed C–C bond-forming reactions, such as Ring-Closing Metathesis (RCM) and the Heck reaction, and subsequent oxidative aromatization through the use either of chloranil or of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ).

In particular, the method is well suited for the synthesis of 2,5-disubstituted furans, including unsymmetrical 2,5-diaryl furans, which play an increasingly important role in medicinal chemistry and drug discovery.

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