Chemoselective Suzuki-Miyaura reactions of 4-bromo-3-O-triflyl-estrone. Synthesis and atropisomerism of arylated estrones

Stefan Jopp, Tina Wallaschkowski, Peter Ehlers, E. Frank, G. Schneider, J. Wölfling, E. Mernyák, Alexander Villinger, Peter Langer

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

4-Bromo-3-O-triflyl-estrone has been synthesized in 2 steps from estrone and was successfully employed in chemoselective palladium catalysed Suzuki-Miyaura reactions. Mono- and bis-arylations were carried out selectively by variation of ligands and solvents. Overall 19 derivatives of mono- and bis-arylated estrones were synthesized under optimized conditions in high yields. Various products showed atropisomerism which was studied in detail by NMR spectroscopy.

Original languageEnglish
Pages (from-to)2825-2836
Number of pages12
JournalTetrahedron
Volume74
Issue number23
DOIs
Publication statusPublished - Jun 7 2018

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Estrone
Palladium
Nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
Ligands
Derivatives

Keywords

  • Chemoselectivity
  • Cross-coupling reactions
  • Palladium
  • Palladium
  • Steroids

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Chemoselective Suzuki-Miyaura reactions of 4-bromo-3-O-triflyl-estrone. Synthesis and atropisomerism of arylated estrones. / Jopp, Stefan; Wallaschkowski, Tina; Ehlers, Peter; Frank, E.; Schneider, G.; Wölfling, J.; Mernyák, E.; Villinger, Alexander; Langer, Peter.

In: Tetrahedron, Vol. 74, No. 23, 07.06.2018, p. 2825-2836.

Research output: Contribution to journalArticle

Jopp, Stefan ; Wallaschkowski, Tina ; Ehlers, Peter ; Frank, E. ; Schneider, G. ; Wölfling, J. ; Mernyák, E. ; Villinger, Alexander ; Langer, Peter. / Chemoselective Suzuki-Miyaura reactions of 4-bromo-3-O-triflyl-estrone. Synthesis and atropisomerism of arylated estrones. In: Tetrahedron. 2018 ; Vol. 74, No. 23. pp. 2825-2836.
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