Oxidative biaryl coupling of thiophenes and thiazoles with arylboronic acids through palladium catalysis: Otherwise difficult C4-selective C-H arylation enabled by boronic acids

  • Kirchberg S
  • Tani S
  • Ueda K
 et al. 
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Abstract

It adds up to 4! Thiophenes and thiazoles can be arylated in the 4- rather than the expected 5-position in a new CH 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.

Author-supplied keywords

  • Boronic acids
  • C-H arylation
  • Palladium
  • Regioselectivity
  • Thiazoles
  • Thiophenes

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Authors

  • Sylvia Kirchberg

  • Satoshi Tani

  • Kirika Ueda

  • Junichiro Yamaguchi

  • Armido Studer

  • Kenichiro Itami

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