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Keywords:

  • cross-coupling;
  • metalation;
  • pyridine;
  • zinc
Thumbnail image of graphical abstract

Either ZnCl2, Sc(OTf)3 , or BF3⋅OEt2 can promote the palladium-catalyzed arylation of methylpyridines and related heterocycles (see example). The complexation of the Lewis acid to the nitrogen atom in the heterocycle facilitates the reductive elimination, leading to various arylated pyridines in high yields. BF3⋅OEt2 was also found to promote highly regioselective metalations in the case of 2,4-lutidine.