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  • 4.
    Malmgren, Joel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of Alkynyl(aryl)iodonium salts from TMS-alkynesManuscript (preprint) (Other academic)
  • 5.
    Malmgren, Joel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Unsymmetrical Diaryliodonium Salts: Development and Chemoselectivity studies2013Licentiate thesis, comprehensive summary (Other academic)
    Abstract [en]

    The first part describes a chemoselectivity study on diaryliodonium salts where oxygen, nitrogen and carbon nucleophiles have been arylated. Twelve different unsymmetric phenyl(aryl)iodonium salts were designed with a systematic variation of the steric and electronic properties of the aryl group. The chemoselectivity varies greatly between the nucleophiles but several “dummy” aryl groups were identified where selective transfer of the phenyl moiety was consequently observed. HRMS studies of the salts revealed an interesting ligand exchange between the aryl groups of the iodine under certain conditions. This will aid the understanding of the mechanism operating in diaryliodonium salt arylation reactions. The results will facilitate the design of catalytic systems employing diaryliodonium salts, as well as help in search for applications with polymer-bound salts.

    The second part of the thesis describes the development of a new synthetic route towards unsymmetric diaryliodonium salts containing one heteroaryl moiety. The substrate scope of the facile one-pot protocol involves salts containing dummy groups with large steric bulk as well as electron-rich aryl groups. The utility of the salts are demonstrated in the arylation of both phenols and malonates where selective transfer of the heteroaryl moiety was consistently observed

  • 6.
    Malmgren, Joel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Nagendiran, Anuja
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tai, Cheuk-Wai
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    C-2 Selective Arylation of Indoles with Heterogeneous Nanopalladium and Diaryliodonium Salts2014In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, no 42, p. 13531-13535Article in journal (Refereed)
    Abstract [en]

    A simple and efficient method to prepare synthetically useful 2-arylindoles is presented, using a heterogeneous Pd catalyst and diaryliodonium salts in water under mild conditions. A remarkably low leaching of metal catalyst was observed under the applied conditions. The developed protocol is highly C-2 selective and tolerates structural variations both in the indole and in the diaryliodonium salt. Arylations of both NH indoles and N-protected indoles with ortho-substituted, electron-rich, electron-deficient, or halogenated diaryliodonium salts were achieved to give the desired products in high to excellent isolated yields within 6 to 15 h at room temperature or 40 °C.

  • 7.
    Malmgren, Joel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Santoro, Stefano
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jalalian, Nazli
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Himo, Fahmi
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Arylation with Unsymmetrical Diaryliodonium Salts: A Chemoselectivity Study2013In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 19, no 31, p. 10334-10342Article in journal (Refereed)
    Abstract [en]

    Phenols, anilines, and malonates have been arylated under metal-free conditions with twelve aryl(phenyl)iodonium salts in a systematic chemoselectivity study. A new “anti-ortho effect” has been identified in the arylation of malonates. Several “dummy groups” have been found that give complete chemoselectivity in the transfer of the phenyl moiety, irrespective of the nucleophile. An aryl exchange in the diaryliodonium salts has been observed under certain arylation conditions. DFT calculations have been performed to investigate the reaction mechanism and to elucidate the origins of the observed selectivities. These results are expected to facilitate the design of chiral diaryliodonium salts and the development of catalytic arylation reactions that are based on these sustainable and metal-free reagents.

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