Suzuki aryl cross-coupling chemistry using derivatives of 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Alex J. Roche, Belgin Canturk

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

An exploration into the scope of Suzuki aryl cross-coupling chemistry using derivatives of 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane is reported. The coupling of 4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane with various aryl boronic acids and boronic acid pinacol esters was successful, with the exception of very sterically demanding systems, such as mesityl. The synthesis of the previously unreported 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophanyl-4- boronic acid is described, together with various Suzuki aryl cross-coupling reactions of this new system. Using standard Suzuki methodology, it was possible to prepare dicyclophanes bearing two octafluoro[2.2]paracyclophane units separated by both one and two benzene rings.

Original languageEnglish (US)
Pages (from-to)481-488
Number of pages8
JournalJournal of Fluorine Chemistry
Volume126
Issue number4
DOIs
StatePublished - Apr 2005

ASJC Scopus subject areas

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

Keywords

  • Dicyclophane
  • OFP
  • Octafluoro[2.2]paracyclophane
  • Paracyclophane
  • Suzuki aryl cross-coupling

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