Exclusive 5-exo-dig hydroarylation of o-alkynyl biaryls proceeding via C-H activation pathway

Natalia Chernyak, Vladimir Gevorgyan

Research output: Contribution to journalArticle

150 Citations (Scopus)

Abstract

The first example of the palladium-catalyzed exclusive 5-exo-dig hydroarylation of o-alkynyl biaryls has been demonstrated. In contrast to the reported earlier carbocyclizations proceeding via the Friedel-Crafts mechanism, this hydroarylation efficiently proceeds with electron-neutral and electron-deficient arenes, producing fluorene frameworks with defined stereochemistry of the double bond. On the basis of the high reactivity of electron-deficient arenes toward cyclization, high values of inter- and intramolecular kinetic isotope effects, and the exclusive cis-selectivity of cyclization, a mechanism involving a C-H activation motif has been proposed for this transformation.

Original languageEnglish (US)
Pages (from-to)5636-5637
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number17
DOIs
StatePublished - Apr 30 2008
Externally publishedYes

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Chemical activation
Cyclization
Electrons
Stereochemistry
Palladium
Isotopes
Kinetics
fluorene

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Exclusive 5-exo-dig hydroarylation of o-alkynyl biaryls proceeding via C-H activation pathway. / Chernyak, Natalia; Gevorgyan, Vladimir.

In: Journal of the American Chemical Society, Vol. 130, No. 17, 30.04.2008, p. 5636-5637.

Research output: Contribution to journalArticle

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