Skip to main navigation Skip to search Skip to main content

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
  • *Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

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
StatePublished - 27 Mar 2013
Externally publishedYes

Bibliographical note

Funding Information:
Financial support by the Higher Education Commission Pakistan and by the DAAD (scholarships for S.A. and K.S.) is gratefully acknowledged. Financial support by the European Social Fund (EFRE program) is also acknowledged. The work was also supported by the TÁMOP-4.2.1/B-09/KONV-2010-007 project. The project is implemented through the New Hungary Development Plan, co-financed by the European Social Fund and the European Regional Development Fund.

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Synthesis of 2,6-diaryl-3-(trifluoromethyl)pyridines by regioselective Suzuki-Miyaura reactions of 2,6-dichloro-3-(trifluoromethyl)pyridine'. Together they form a unique fingerprint.

Cite this