Palladium-catalyzed reactions of vinyl bromides with disubstituted alkynes: a new synthesis of fulvenes

Lee J. Silverberg, Guangzhong Wu, Arnold L. Rheingold, Richard F. Heck

Research output: Contribution to journalArticle

31 Scopus citations

Abstract

The palladium-catalyzed reaction of vinylic bromides with disubstituted acetylenes at 100°C in the presence of triethylamine produces penta- or hexa-substituted fulvenes in low to moderate yields. Reactions with 3-hexyne under the same conditions usually yield dialkylidenecyclopentenes as products, apparently by rearrangement of the expected fulvenes. Fulvenes formed from the reaction of disubstituted alkynes with Z-2-bromovinyl ethyl ether can be hydrolyzed to produce cyclopentadiene carboxaldehydes.

Original languageEnglish (US)
Pages (from-to)411-420
Number of pages10
JournalJournal of Organometallic Chemistry
Volume409
Issue number3
DOIs
StatePublished - Jun 4 1991

All Science Journal Classification (ASJC) codes

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

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