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  • 1.
    Jalalian, Nazli
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Development and Applications of Hypervalent Iodine Compounds: Powerful Arylation and Oxidation Reagents2012Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    The first part of this thesis describes the efficient synthesis of several hypervalent iodine(III) compounds. Electron-rich diaryliodonium salts have been synthesized in a one-pot procedure, employing mCPBA as the oxidant. Both symmetric and unsymmetric diaryliodonium tosylates can be isolated in high yields. An in situ anion exchange also enables the synthesis of previously unobtainable diaryliodonium triflates.

    A large-scale protocol for the synthesis of a derivative of Koser’s reagent, that is an isolable intermediate in the diaryliodonium tosylate synthesis, is furthermore described. The large-scale synthesis is performed in neat TFE, which can be recovered and recycled. This is very desirable from an environmental point of view.

    One of the few described syntheses of enantiopure diaryliodonium salts is discussed. Three different enantiopure diaryliodonium salts bearing electron-rich substituents are synthesized in moderate to high yields. The synthesis of these three salts shows the challenge in the preparation of electron-rich substituted unsymmetric salts.

    The second part of the thesis describes the application of both symmetric and unsymmetric diaryliodonium salts in organic synthesis. A metal-free efficient and fast method for the synthesis of diaryl ethers from diaryliodonium salts has been developed. The substrate scope is wide as both the phenol and the diaryliodonium salt can be varied. Products such as halogenated ethers, ortho-substituted ethers and bulky ethers, that are difficult to obtain with metal-catalyzed procedures, are readily prepared. The mild protocol allows arylation of racemization-prone a-amino acid derivatives without loss of enantiomeric excess.

    A chemoselectivity investigation was conducted, in which unsymmetric diaryliodonium salts were employed in the arylation of three different nucleophiles in order to understand the different factors that influence which aryl moiety that is transferred to the nucleophile.

  • 2.
    Jalalian, Nazli
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis and applications of diaryliodonium salts2010Licentiate thesis, comprehensive summary (Other academic)
  • 3.
    Jalalian, Nazli
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ishikawa, Eloisa E.
    Universidade de Sao Paulo, Instituto de Quimica.
    Silva Jr., Luiz F.
    Universidade de Sao Paulo, Instituto de Quimica.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Room temperature, metal-free synthesis of diaryl ethers with use of diaryliodonium salts2011In: Abstracts of Papers, 242nd ACS National Meeting & Exposition, Denver, CO, United States, August 28-September 1, 2011, American Chemical Society , 2011Conference paper (Other academic)
    Abstract [en]

    Diaryl ethers are common structural features in numerous natural products and biol. active compds.  Despite more than a century of immense focus on finding efficient synthetic routes to this compd. class, diaryl ethers remain difficult to obtain.  Routes that are catalytic in copper have been developed, but high catalyst loadings, excess reagents, elevated temps. and long reaction times are still needed.  Pd-catalyzed cross-couplings of phenols and aryl halides at temps. up to 100 °C have recently been reported to give high yields of diaryl ethers.  Diaryliodonium salts are non-toxic alternatives to transition metals in the synthesis of diaryl ethers and we have recently developed effective synthetic routes to these salts.  Herein we report a fast, high-yielding synthesis of diaryl ethers.  The reaction conditions are mild, metal-free, and avoid the use of halogenated solvents, additives, or excess reagents.  Precautions to avoid air or moisture are not needed.  The scope includes ortho- and halo-substituted diaryl ethers, which are difficult to obtain by metal-catalyzed protocols .

  • 4.
    Jalalian, Nazli
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Asymmetric α-arylation of carbonyl compounds with chiral diaryliodonium salts2009In: Abstracts of Papers, 238th ACS National Meeting, Washington, DC, United States, August 16-20, 2009, Washington, D.C.: American Chemical Society , 2009Conference paper (Other academic)
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