Copper(II) Fluoride a New Efficient Promoter of Chan-Lam-Evans Coupling

Authors

  • Balázs Komjáti
    Affiliation

    Department of Organic Chemistry and Technology Faculty of Chemical Technology and Biotechnology Budapest University of Technology and Economics H-1111 Budapest Szent Gellért tér 4

  • Bianka Szokol
    Affiliation

    Department of Organic Chemistry and Technology Faculty of Chemical Technology and Biotechnology Budapest University of Technology and Economics H-1111 Budapest Szent Gellért tér 4, Hungary

  • László Poppe
    Affiliation

    Department of Organic Chemistry and Technology Faculty of Chemical Technology and Biotechnology Budapest University of Technology and Economics H-1111 Budapest Szent Gellért tér 4

  • József Nagy
    Affiliation

    Department of Organic Chemistry and Technology Faculty of Chemical Technology and Biotechnology Budapest University of Technology and Economics H-1111 Budapest Szent Gellért tér 4

https://doi.org/10.3311/PPch.7835

Abstract

The Chan-Lam-Evans coupling is the copper(II) acetate promoted reaction of phenols and boronic acids producing diaryl ethers. In this paper a modification of the original reaction is reported using copper(II) fluoride reagent which gives higher yields than copper(II) acetate. The most significant increase in yield was observed in formation of sterically hindered phenols. We hypothesize that fluoride ions help to cleave the boron-carbon bond. The novel method is suitable for selective, efficient and economical synthesis of diaryl ether compounds under mild conditions.

Keywords:

cross coupling, copper(II) fluoride, boronic acid, diaryl ether

Published Online

2015-02-18

How to Cite

Komjáti, B., Szokol, B., Poppe, L., Nagy, J. “Copper(II) Fluoride a New Efficient Promoter of Chan-Lam-Evans Coupling”, Periodica Polytechnica Chemical Engineering, 59(4), pp. 243–246, 2015. https://doi.org/10.3311/PPch.7835

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Section

Articles