Palladium catalyzed cross- and homo-coupling reactions of 4-Halo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophanes with various organometallic reagents

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Abstract

An investigation of palladium catalyzed Kumada type reactions between various Grignard reagents and mono-substituted octafluoroparacyclophane derivatives revealed that by varying the reaction temperature, and mode of addition of the Grignard reagent, it was possible to influence whether the major product was the cross-coupled, or the homo-coupled (reductive dimer) paracyclophane product. This provides an improved methodology to prepare aryl substituted paracyclophanes, and additionally an alternative route to the unusual and rare di-cyclophane skeleton. Analogous reactions with alkyl lithium reagents were also explored, resulting in the generation of some previously unreported octafluoroparacyclophane products.

Original languageEnglish (US)
Pages (from-to)1-5
Number of pages5
JournalJournal of Fluorine Chemistry
Volume175
DOIs
StatePublished - Jul 2015

All Science Journal Classification (ASJC) codes

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

Keywords

  • Dicyclophane
  • Kumada reaction
  • Octafluoro[2.2]paracyclophane

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