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Keywords:

  • boronic acids;
  • C[BOND]H arylation;
  • palladium;
  • regioselectivity;
  • thiazoles;
  • thiophenes
Thumbnail image of graphical abstract

It adds up to 4! Thiophenes and thiazoles can be arylated in the 4- rather than the expected 5-position in a new C[BOND]H functionalization reaction (see scheme; TEMPO: 2,2,6,6-tetramethylpiperidine-N-oxyl). The boronic acid proved to be the key to achieving the otherwise difficult C4 selectivity. The method was applied to a concise synthesis of a key pharmacological structure with potential for treatment of Alzheimer's disease.