Chemo-, regio- and stereoselective tricyclohexylphosphine-catalyzed [3+2] cycloaddition of enynes with [60]fullerene initiated by 1,4-michael addition: Synthesis of cyclopenteno[60]fullerenes and their electrochemical properties

Po Yen Tseng, Shih-Ching Chuang*

*Corresponding author for this work

Research output: Contribution to journalArticle

18 Scopus citations

Abstract

Herein we demonstrate a tricyclohexylphosphine-catalyzed cycloaddition of (E)- or (Z)-alkyl 5-substituted phenylpent-2-en-4-ynoates with [60]fullerene to give cyclopentenofullerenes in good to excellent yields, through initial chemo- and regioselective 1,4-addition of phosphines at the b-carbon of the enyne substrates. The nucleophilic addition pattern of P (cHx)3 is found to be different from that of Gilman or Grignard reagents toward the studied enynes. The resulting cyclopentenofullerenes, characterized with spectrometric methods and single crystal X-ray diffraction analysis, exhibit comparable or higher LUMO energy levels than a typical n-type material, [6,6]-phenyl-C61-butyric acid methyl ester (PCBM).

Original languageEnglish
Pages (from-to)2165-2171
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume355
Issue number11-12
DOIs
StatePublished - 12 Aug 2013

Keywords

  • Cycloaddition
  • Enynes
  • Fullerenes
  • Michael addition
  • Phosphanes

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