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  • 1.
    Bermejo Gómez, Antonio
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cortes, Miguel Angel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lübcke, Marvin
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Karolinska Institutet, Sweden.
    Johansson, Magnus J.
    Halldin, Christer
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Karolinska Insitutet, Sweden.
    Schou, Magnus
    Efficient DBU accelerated synthesis of F-18-labelled trifluoroacetamides2016In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 52, no 97, p. 13963-13966Article in journal (Refereed)
    Abstract [en]

    Nucleophilic F-18-fluorination of bromodifluoromethyl derivatives was performed using [F-18] Bu4NF in the presence of DBU(1,8-diazabicyclo[5.4.0]undec-7-ene). This novel procedure provided a diverse set of [F-18] trifluoroacetamides in good to excellent radiochemical conversions. A mechanism where DBU acts as organomediator in this transformation is proposed.

  • 2.
    Bermejo Gómez, Antonio
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cortes, Miguel Angel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lübcke, Marvin
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Karolinska Intitutet, Sweden.
    Johansson, Magnus J.
    Schou, Magnus
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Karolinska Intitutet, Sweden.
    Synthesis of trifluoromethyl moieties by late-stage copper (I) mediated nucleophilic fluorination2017In: Journal of fluorine chemistry, ISSN 0022-1139, E-ISSN 1873-3328, Vol. 194, p. 51-57Article in journal (Refereed)
    Abstract [en]

    The nucleophilic fluorination of bromodifluoromethyl derivatives mediated by the complex (PPh3)(3)CuF is described. Under the reaction conditions, different trifluoroacetates, trifluorolcetones, trifluoroarenes and trifluoroacetamides were obtained in good yields.

  • 3.
    Lübcke, Marvin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bezhan, Dina
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Trifluoromethylthiolation-arylation of diazocarbonyl compounds by modified Hooz multicomponent coupling2019In: Chemical Science, ISSN 2041-6520, E-ISSN 2041-6539, Vol. 10, no 23, p. 5990-5995Article in journal (Refereed)
    Abstract [en]

    A new Zn-mediated trifluoromethylthiolation-based bifunctionalization reaction is developed. In this process, simultaneous C-SCF3 and C-C bond formation takes place in a multicomponent reaction, in which an aryl and a SCF3 group arise from different reagents. Our studies show that the reaction mechanism is similar to the Hooz multicomponent coupling. The process involves in situ generation of BAr3, which reacts with a diazocarbonyl compound, and the reaction is terminated by an electrophilic SCF3 transfer. The reaction can also be extended to fluorination based bifunctionalization which proceeds with somewhat lower yield than the analogous trifluoromethylthiolation reaction.

  • 4.
    Lübcke, Marvin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Karolinska Institutet, Sweden.
    Yuan, Weiming
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Karolinska Institutet, Sweden.
    Trifluoromethylthiolation-Based Bifunctionalization of Diazocarbonyl Compounds by Rhodium Catalysis2017In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 19, no 17, p. 4548-4551Article in journal (Refereed)
    Abstract [en]

    A new Rh-catalyzed, three-component reaction for the oxytrifluoromethylthiolation of alpha-diazoketones was developed. The SCF3 functionality was introduced using a stable dibenzenesulfonimide reagent under mild conditions. Alcohols, acetals, and ethers were used as the alkoxy sources. Cyclic ethers underwent a trifunctionalization reaction through the introduction of SCF3, OR, and N(SO2Ph)(2) substituents in a single step.

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