Synthesis of 2,6-diaryl-3-(trifluoromethyl)pyridines by regioselective Suzuki-Miyaura reactions of 2,6-dichloro-3-(trifluoromethyl)pyridine

Shahzad Ahmed, Muhammad Sharif, Khurram Shoaib, Sebastian Reimann, Jamshed Iqbal, Tamás Patonay, Anke Spannenberg, Peter Langer

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Abstract

The Suzuki-Miyaura reaction of 2,6-dichloro-3-(trifluoromethyl)pyridine with 1 equiv of arylboronic acids resulted in site-selective formation of 2-aryl-6-chloro-3-(trifluoromethyl)pyridine. Due to electronic reasons, the reaction takes place at the sterically more hindered position. The one-pot reaction with two different arylboronic acids afforded 2,6-diaryl-3- (trifluoromethyl)pyridine containing two different aryl substituents. The reactions proceeded smoothly in the absence of phosphane ligands.

Original languageEnglish
Pages (from-to)1669-1672
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number13
DOIs
Publication statusPublished - Mar 27 2013

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Keywords

  • Catalysis
  • Organofluorine compounds
  • Palladium
  • Regioselectivity
  • Suzuki-Miyaura reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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