Gold catalysis: Non-spirocyclic intermediates in the conversion of furanynes by the formal insertion of an alkyne into an aryl-alkyl C-C single bond

A. Stephen K. Hashmi, Tobias Häffner, Weibo Yang, Sreekumar Pankajakshan, Sascha Schäfer, Lara Schultes, Frank Rominger, Wolfgang Frey

Research output: Contribution to journalArticle

Abstract

It takes al-kynes: The formation of furyl-substituted heterocycles from furanynes with donor groups on the furan-alkyne tether and mechanistic control experiments indicate the involvement of open-chained carbenium ions in the overall insertion of an alkyne into a C-C bond, rather than the usual spirocyclic intermediates (see scheme).

Original languageEnglish (US)
Pages (from-to)10480-10486
Number of pages7
JournalChemistry - A European Journal
Volume18
Issue number34
DOIs
StatePublished - Aug 20 2012

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Keywords

  • alkynes
  • carbocations
  • furans
  • gold
  • heterocycles
  • reaction mechanisms

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Hashmi, A. S. K., Häffner, T., Yang, W., Pankajakshan, S., Schäfer, S., Schultes, L., Rominger, F., & Frey, W. (2012). Gold catalysis: Non-spirocyclic intermediates in the conversion of furanynes by the formal insertion of an alkyne into an aryl-alkyl C-C single bond. Chemistry - A European Journal, 18(34), 10480-10486. https://doi.org/10.1002/chem.201200306