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, T. Patonay, Anke Spannenberg, Peter Langer

Research output: Contribution to journalArticle

15 Citations (Scopus)

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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phosphine
Acids
Ligands
3-trifluoromethylpyridine

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of 2,6-diaryl-3-(trifluoromethyl)pyridines by regioselective Suzuki-Miyaura reactions of 2,6-dichloro-3-(trifluoromethyl)pyridine. / Ahmed, Shahzad; Sharif, Muhammad; Shoaib, Khurram; Reimann, Sebastian; Iqbal, Jamshed; Patonay, T.; Spannenberg, Anke; Langer, Peter.

In: Tetrahedron Letters, Vol. 54, No. 13, 27.03.2013, p. 1669-1672.

Research output: Contribution to journalArticle

Ahmed, Shahzad ; Sharif, Muhammad ; Shoaib, Khurram ; Reimann, Sebastian ; Iqbal, Jamshed ; Patonay, T. ; Spannenberg, Anke ; Langer, Peter. / Synthesis of 2,6-diaryl-3-(trifluoromethyl)pyridines by regioselective Suzuki-Miyaura reactions of 2,6-dichloro-3-(trifluoromethyl)pyridine. In: Tetrahedron Letters. 2013 ; Vol. 54, No. 13. pp. 1669-1672.
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AU - Sharif, Muhammad

AU - Shoaib, Khurram

AU - Reimann, Sebastian

AU - Iqbal, Jamshed

AU - Patonay, T.

AU - Spannenberg, Anke

AU - Langer, Peter

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