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  • 1.
    Dey, Chandan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lindstedt, Erik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Wallenberg Research Centre at Stellenbosch University, South Africa.
    Metal-Free C-Arylation of Nitro Compounds with Diaryliodonium Salts2015In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 17, no 18, p. 4554-4557Article in journal (Refereed)
    Abstract [en]

    An efficient, mild, and metal-free arylation of nitro-alkanes with diaryliodonium salts has been developed, giving easy access to tertiary nitro compounds. The reaction proceeds in high yields without the need for excess reagents and can be extended to alpha-arylation of nitroesters. Nitroalkanes were selectively C-arylated in the presence of other easily arylated functional groups, such as phenols and aliphatic alcohols.

  • 2.
    Ghosh, Raju
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lindstedt, Erik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jalalian, Nazli
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Room Temperature, Metal-Free Arylation of Aliphatic Alcohols2014In: ChemistryOpen, ISSN 2191-1363, Vol. 3, no 2, p. 54-57Article in journal (Refereed)
    Abstract [en]

    Diaryliodonium salts are demonstrated as efficient arylating agents of aliphatic alcohols under metal-free conditions. The reaction proceeds at room temperature within 90min to give alkyl aryl ethers in good to excellent yields. Aryl groups with electron-withdrawing substituents are transferred most efficiently, and unsymmetric iodonium salts give chemoselective arylations. The methodology has been applied to the formal synthesis of butoxycaine.

  • 3.
    Lindstedt, Erik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Metal-Free O- and C-Arylation with Diaryliodonium Salts2017Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis concerns the development of metal-free applications using diaryliodonium salts. The first project describes an arylation protocol of allylic and benzylic alcohols in aqueous media. The method proceeds under mild conditions and the ether products were obtained in moderate to good yields. The methodology was also expanded to include arylation of phenols, giving diaryl ethers in good to excellent yields. In the second project, an arylation method that included a wider range of aliphatic alcohols was developed. The scope of accessible alkyl aryl ethers was studied and included a comparative study of phenylation and nitrophenylation of various alcohols. Finally, a formal metal-free synthesis of butoxycain was performed, illustrating the applicability of the developed method.

    The third project focused on the limitations and side reactions occurring in Chapter 2 and 3. First, an approach to access symmetric diaryl ethers via arylation of hydroxide was presented. This reaction gave rise to a number of side products, which we hypothesized to originate from aryne-type intermediates. A mechanism for the formation of these side products was suggested, supported by trapping and deuterium labeling experiments.

    Oxidation of the alcohol to the corresponding ketone was also observed and the mechanism of this interesting side reaction was investigated. The latter was suggested to proceed via an intramolecular oxidation without the involvement of radicals or arynes.

    The fourth project covers a method to synthesize highly sterically congested alkyl aryl ethers via arylation of tertiary alcohols using diaryliodonium salts. The method displayed a broad scope of tertiary alcohols and was also suitable for fluorinated alcohols.

    The final project detailed in this thesis deals with C-arylation with diaryliodonium salts, showcasing nitroalkanes as well as a nitro ester as suitable nucleophiles for metal-free arylation. 

  • 4.
    Lindstedt, Erik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of Aryl Ethers: Metal-Free Arylation of Alcohols using Diaryliodonium Salts2015Licentiate thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis contains two parts showing different metal-free methods to synthesize aryl ethers using hypervalent iodine reagents, more specifically diaryliodonium salts. The first part describes arylation of benzylic and allylic alcohols and phenols in water using the easily accessible base sodium hydroxide. Chemoselectivity of phenols in aqueous media is discussed and limitations of the reaction are presented.

    The second part describes an arylation of aliphatic alcohols at room temperature with short reaction time and no excess of reagents are required. The scope of the methodology was investigated and showed that electron-deficient iodonium salts worked efficiently, but unfortunately electron-rich was not compatible with the reaction conditions. The methodology was applied in a formal synthesis of Butoxycaine.

  • 5.
    Lindstedt, Erik
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ghosh, Raju
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Metal-Free Synthesis of Aryl Ethers in Water2013In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 15, no 23, p. 6070-6073Article in journal (Refereed)
    Abstract [en]

    The first arylation of allylic and benzylic alcohols with diaryliodonium salts is reported. The reaction yields alkyl aryl ethers under mild and metal-free conditions. Phenols are arylated to diaryl ethers in good to excellent yields. The reaction employs diaryliodonium salts and sodium hydroxide in water at low temperature, and excess amounts of the coupling partners are avoided.

  • 6.
    Lindstedt, Erik
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Reitti, Marcus
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    One-Pot Synthesis of Unsymmetric Diaryliodonium Salts from Iodine and Arenes2017In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 82, no 22, p. 11909-11914Article in journal (Refereed)
    Abstract [en]

    The first synthesis of unsymmetric diaryliodonium salts directly from iodine and arenes is presented. The methodology provides diaryliodonium salts with the trimethoxyphenyl (TMP) moiety as dummy group. The protocol avoids the customary use of iodoarenes, which can be both expensive and toxic. Excess reagents are not required, and the reactions are performed under mild conditions. O-Arylations with these TMP salts were demonstrated to be highly chemoselective.

    The full text will be freely available from 2018-08-15 13:00
  • 7.
    Lindstedt, Erik
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stridfeldt, Elin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mild Synthesis of Sterically Congested Alkyl Aryl Ethers2016In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 18, no 17, p. 4234-4237Article in journal (Refereed)
    Abstract [en]

    An efficient and transition-metal-free method is presented to access tertiary alkyl aryl ethers by arylation of tertiary alcohols with ortho-substituted diaryliodonium salts. The scope covers cyclic and acyclic aliphatic, benzylic, allylic, and propargylic tertiary alcohols as well as primary and secondary fluorinated alcohols. The methodology gives access to alkyl aryl ethers of previously unprecedented steric congestion. Furthermore, the versatility of the developed procedure was demonstrated by arylation of the pro-drug mestranol.

  • 8.
    Reitti, Marcus
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Gurubrahamam, Ramani
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Walther, Melanie
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lindstedt, Erik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of Phenols and Aryl Silyl Ethers via Arylation of Complementary Hydroxide Surrogates2018In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 20, no 7, p. 1785-1788Article in journal (Refereed)
    Abstract [en]

    Two transition-metal-free methods to access substituted phenols via the arylation of silanols or hydrogen peroxide with diaryliodonium salts are presented. The complementary reactivity of the two nucleophiles allows synthesis of a broad range of phenols without competing aryne formation, as illustrated by the synthesis of the anesthetic Propofol. Furthermore, silyl-protected phenols can easily be obtained, which are suitable for further transformations.

    The full text will be freely available from 2019-03-14 01:00
  • 9.
    Stridfeldt, Elin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lindstedt, Erik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Reitti, Marcus
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Blid, Jan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Norrby, Per-Ola
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Competing Pathways in O-Arylations with Diaryliodonium Salts: Mechanistic Insights2017In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 23, no 53, p. 13249-13258Article in journal (Refereed)
    Abstract [en]

    A mechanistic study of arylations of aliphatic alcohols and hydroxide with diaryliodonium salts, to give alkyl aryl ethers and diaryl ethers, has been performed using experimental techniques and DFT calculations. Aryne intermediates have been trapped, and additives to avoid by-product formation originating from arynes have been found. An alcohol oxidation pathway was observed in parallel to arylation; this is suggested to proceed by an intramolecular mechanism. Product formation pathways via ligand coupling and arynes have been compared, and 4-coordinated transition states were found to be favored in reactions with alcohols. Furthermore, a novel, direct nucleophilic substitution pathway has been identified in reactions with electron-deficient diaryliodonium salts.

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