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Keywords:

  • copper;
  • cross-coupling;
  • Grignard reaction;
  • palladium;
  • regioselectivity

Abstract

Disubstituted thienyl-, furyl- and pyridylmagnesium derivatives are regioselectively prepared from a Br/Mg exchange of the corresponding dibromo compounds by using either iPrMgClLiCl or hindered arylmagnesium reagents, such as isitylmagnesium bromidelithium chloride (isityl=2,4,6-triisopropyl-phenyl) complexed with a diamine ligand, in difficult cases. The selective functionalisations of these heterocyclic scaffolds by using Negishi cross-coupling reactions, acylations or addition to aldehydes were readily achieved.