Palladium-catalyzed enyne-yne [4 + 2] benzannulation as a new and general approach to polysubstituted benzenes

Vladimir Gevorgyan, Yoshinori Yamamoto

Research output: Contribution to journalReview article

102 Scopus citations

Abstract

Monosubstituted conjugated enynes smoothly underwent [4 + 2] homodimerization in the presence of palladium catalyst to give 4, α- and 2,6-disubstituted styrenes. Analogous cross-cycloaddition of conjugated enynes and diynes afforded a variety of polysubstituted benzenes, including phenol and aniline derivatives. Alkynes and diynes in the presence of a palladium catalyst underwent novel formal [2 + 2 + 2] sequential cyclotrimerization to afford multifunctional benzenes in one step with high degrees of regio- and chemoselectivities. Mechanisms of these novel transformations are discussed.

Original languageEnglish (US)
Pages (from-to)232-247
Number of pages16
JournalJournal of Organometallic Chemistry
Volume576
Issue number1-2
DOIs
StatePublished - Mar 15 1999
Externally publishedYes

Keywords

  • Alkynes
  • Benzene
  • Cycloaddition
  • Diynes
  • Enynes
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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