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

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Percy, Jonathan M. and Emerson, Helena and Fyfe, James W. B. and Kennedy, Alan R. and Maciuk, Sergej and Orr, David and Rathouska, Lucie and Redmond, Joanna M. and Wilson, Peter G. (2016) Modular construction of fluoroarenes from a new difluorinated building block via cross-coupling/electrocyclisation/ dehydrofluorination reactions. Chemistry - A European Journal, 22 (34). pp. 12166-12175. ISSN 1521-3765 (https://doi.org/10.1002/chem.201601584)

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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.

ORCID iDs

Percy, Jonathan M. ORCID logoORCID: https://orcid.org/0000-0001-8636-2704, Emerson, Helena ORCID logoORCID: https://orcid.org/0000-0001-8710-0511, Fyfe, James W. B. ORCID logoORCID: https://orcid.org/0000-0001-8501-9197, Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Maciuk, Sergej, Orr, David ORCID logoORCID: https://orcid.org/0000-0002-7212-9837, Rathouska, Lucie, Redmond, Joanna M. and Wilson, Peter G.;
  • Item type:Article
    ID code:56649
    Dates:
    Date
    Event
    31 August 2016
    Published
    14 July 2016
    Published Online
    8 June 2016
    Accepted
    Notes:This is the peer reviewed version of the following article: J. M. Percy, H. Emerson, J. W. B. Fyfe, A. R. Kennedy, S. Maciuk, D. Orr, L. Rathouská, J. M. Redmond, P. G. Wilson, Chem. Eur. J. 2016, 22, 12166., which has been published in final form at https://doi.org/10.1002/chem.201601584. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:13 Jun 2016 15:48
    Last modified:20 Dec 2024 01:28
    Related URLs:
    URI:https://strathprints.strath.ac.uk/id/eprint/56649
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