Modular construction of fluoroarenes from a new difluorinated building block via cross-coupling/electrocyclisation/ dehydrofluorination reactions

Jonathan M. Percy, Helena Emerson, James W. B. Fyfe, Alan R. Kennedy, Sergej Maciuk, David Orr, Lucie Rathouska, Joanna M. Redmond, Peter G. Wilson

Research output: Contribution to journalArticle

3 Citations (Scopus)
59 Downloads (Pure)

Abstract

Palladium-catalysed coupling reactions based on a novel and easy-to-synthesise difluorinated organotrifluoroborate were used to assemble precursors to 6π-electrocyclisations of three different types. Electrocyclisations took place at temperatures between 90 and 240 oC, depending on the central component of the π-system; non-aromatic trienes were most reactive, but even systems which required the temporary dearomatisation of two arenyl sub-units underwent electrocyclisation, albeit at elevated temperatures. Photochemical conditions were effective for these more demanding reactions. The package of methods delivered a structurally-diverse set of fluorinated arenes, spanning a 20 kcal mol-1 range of reactivity, by a flexible route.
Original languageEnglish
Pages (from-to)12166-12175
Number of pages12
JournalChemistry - A European Journal
Volume22
Issue number34
Early online date14 Jul 2016
DOIs
Publication statusPublished - 31 Aug 2016

Keywords

  • electrocyclic reactions
  • density functional calculations
  • cross-coupling
  • fluorine
  • palladium

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