Simple Access to 2-Arylpyridines

  • Author: European Journal of Inorganic Chemistry
  • Published Date: 14 September 2012
  • Source / Publisher: European Journal of Inorganic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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2-Arylpyridine ligands are important building blocks for preparing materials with a variety of applications. For example, the electronic properties of cyclometallated Au, Ir, Pt, or Ru complexes that bear 2-phenylpyridine ligands can be tuned by introducing appropriate substituents, including heteroaryl groups, at various positions. However, the synthesis of such functionalized products is not always straightforward. Palladium-catalyzed direct arylation of heteroaryl derivatives with aryl halides has proven to be a very powerful method for the synthesis of a wide variety of arylated heteroarenes. However, palladium-catalyzed direct arylation of polyhalopyridines had not been investigated.

Henri Doucet and co-workers, University of Rennes, France, studied the conditions for the sequential direct monoarylation at C3, C4, or C5, of bromo-2-chloropyridines with a variety of heteroarenes, followed by arylation at the C2 position of the pyridyl ring by means of Suzuki coupling with use of a relatively low loading (1 mol %) of an air-stable palladium catalyst associated with a cheap and nontoxic base.

Simple Access to 2-Arylpyridines

The results indicated that the commercially available catalyst was very effective, and this new procedure presents an improvement with respect to previous methods.

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