4.5 Article

Pd(OAc)2/p-benzoquinone-catalyzed anaerobic electrooxidative homocoupling of arylboronic acids, arylboronates and aryltrifluoroborates in DMF and/or water

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2008, Issue 27, Pages 4567-4570

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200800631

Keywords

palladium; homocoupling; boron; borates; electrooxidation

Funding

  1. Centre National de la Recherche Scientifique [UMR CNRS-ENS-UPMC 8640]
  2. Ministere de la Recherche (Ecole Normale Superieure)

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A new anaerobic electrooxidative homocoupling of arylboronic acids, arylboronates and aryltrifluoroborates was developed in the presence of catalytic amounts of Pd(OAc)(2) and p-benzoquinone, which serves as a redox mediator for the oxidation of transient Pd-0 to the active Pd-II species. The homocoupling was performed in DMF, DMF/water or in pure water. This electrochemical process avoids the use of a stoichiometric amount of chemical oxidants and subsequent formation of co- and by-products. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

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