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  • 1.
    Akkarasamiyo, Sunisa
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Margalef, Jèssica
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Samec, Joseph S. M.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction of Naphthyl and Quinolyl Alcohols with Boronic Acids2019In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 21, no 12, p. 4782-4787Article in journal (Refereed)
    Abstract [en]

    A nickel-catalyzed C(sp(3))-C(sp(2)) Suzuki cross-coupling of arylboronic acids and (hetero)naphthyl alcohols has been developed. A Ni(dppp) Cl-2 complex showed the highest efficiency and broadest substrate scope. High functional group tolerance has been achieved where 35 compounds could be generated in good to excellent yields, including both primary and secondary benzylic alcohols. Mechanistic studies using multiple NMR techniques as well as ESI-HRMS showed that the C-O cleavage is facilitated by an activation of the benzylic alcohol through formation of a boronic ester intermediate.

  • 2.
    Akkarasamiyo, Sunisa
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sawadjoon, Supaporn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Orthaber, Andreas
    Samec, Joseph S. M.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tsuji-Trost Reaction of Non-Derivatized Allylic Alcohols2018In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 24, no 14, p. 3488-3498Article in journal (Refereed)
    Abstract [en]

    Palladium-catalyzed allylic substitution of non-derivatized enantioenriched allylic alcohols with a variety of uncharged N-, S-, C- and O-centered nucleophiles using a bidentate BiPhePhos ligand is described. A remarkable effect of the counter ion (X) of the XPd[kappa(2)-BiPhePhos][kappa(3)-C3H5] was observed. When ClPd[kappa(2)-BiPhePhos][eta(3)-C3H5] (complexI) was used as catalyst, non-reproducible results were obtained. Study of the complex by X-ray crystallography, (PNMR)-P-31 spectroscopy, and ESI-MS showed that a decomposition occurred where one of the phosphite ligands was oxidized to the corresponding phosphate, generating ClPd[kappa(1)-BiPhePhosphite-phosphate][eta(3)-C3H5] species (complexII). When the chloride was exchanged to the weaker coordinating OTf- counter ion the more stable Pd[kappa(2)-BiPhePhos][eta(3)-C3H5](+)+[OTf] (-) (complexIII) was formed. ComplexIII performed better and gave higher enantiospecificities in the substitution reactions. ComplexIII was evaluated in Tsuji-Trost reactions of stereogenic non-derivatized allylic alcohols. The desired products were obtained in good to excellent yields (71-98%) and enantiospecificities (73-99%) for both inter- and intramolecular substitution reactions with only water generated as a by-product. The methodology was applied to key steps in total synthesis of (S)-cuspareine and (+)-lentiginosine. A reaction mechanism involving a palladium hydride as a key intermediate in the activation of the hydroxyl group is proposed in the overall transformation.

  • 3. Gupta, Arvind Kumar
    et al.
    Akkarasamiyo, Sunisa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Orthaber, Andreas
    Rich Coordination Chemistry of pi-Acceptor Dibenzoarsole Ligands2017In: Inorganic Chemistry, ISSN 0020-1669, E-ISSN 1520-510X, Vol. 56, no 8, p. 4504-4511Article in journal (Refereed)
    Abstract [en]

    A series of dibenzoarsole (also known as 9-arsafluorene) derivatives have been prepared, and their coordination chemistry has been investigated. The different ligand topology and the arsenic substituents govern the reactivity of the ligands. We report various crystal structures of palladium and platinum complexes derived from this family of ligands. The biphenyl backbone of the bridged bidentate ligands allows very flexible coordination. We have also studied the application of an allylic Pd complex in nucleophilic substitution reactions, revealing that the benzoarsole substituent is susceptible to metal insertion.

  • 4.
    Rukkijakan, Thanya
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Akkarasamiyo, Sunisa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sawadjoon, Supaporn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Samec, Joseph S. M.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Pd-Catalyzed Substitution of the OH Group of Nonderivatized Allylic Alcohols by Phenols2018In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 83, no 7, p. 4099-4104Article in journal (Refereed)
    Abstract [en]

    Nonactivated phenols have been employed as nucleophiles in the allylation of nonderivatized allylic alcohols to generate allylated phenolic ethers with water as the only byproduct. A Pd[BiPhePhos] catalyst was found to be reactive to give the O-allylated phenols in good to excellent yields in the presence of molecular sieves. The reactions are chemo-selective in which the kinetically favored O-allylated products are formed exclusively over the thermodynamically favored C-allylated products.

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