Synthesis of fluorenes via the palladium-catalyzed 5-exo-dig annulation of o-alkynylbiaryls

Natalia Chernyak, Vladimir Gevorgyan

Research output: Contribution to journalArticle

62 Citations (Scopus)

Abstract

The direct palladium-catalyzed intramolecular hydro arylation of o-alkynylbiaryls proceeded in a highly stereoselective manner producing fluorenes 2, the products of 5-exo-dig cyclization, in excellent yields. The cascade intermolecular arylation, incorporated in this transformation, allowed for the efficient synthesis of fully substituted fluorenes 12. These cyclizations proceed more rapidly with electron-deficient benzene rings which, in combination with a substantial isotope effect observed, strongly supports a C-H activation mechanism for the key annulation step.

Original languageEnglish (US)
Pages (from-to)1101-1114
Number of pages14
JournalAdvanced Synthesis and Catalysis
Volume351
Issue number7-8
DOIs
StatePublished - May 1 2009
Externally publishedYes

Fingerprint

Fluorenes
Cyclization
Palladium
Benzene
Isotopes
Chemical activation
Electrons

Keywords

  • Alkynes
  • Annulations
  • Arylation
  • C-H activation
  • Palladium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Synthesis of fluorenes via the palladium-catalyzed 5-exo-dig annulation of o-alkynylbiaryls. / Chernyak, Natalia; Gevorgyan, Vladimir.

In: Advanced Synthesis and Catalysis, Vol. 351, No. 7-8, 01.05.2009, p. 1101-1114.

Research output: Contribution to journalArticle

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