Articles producció científicaQuímica Analítica i Química Orgànica

Phosphine-Free Suzuki-Miyaura Cross-Coupling in Aqueous Media Enables Access to 2-C-Aryl-Glycosides

  • Identification data

    Identifier:  imarina:9297389
    Handle: https://hdl.handle.net/20.500.11797/imarina9297389
    Authors:  Cobo, Isidro; Matheu, M Isabel; Castillon, Sergio; Boutureira, Omar; Davis, Benjamin G
    Abstract:
    A general strategy for the synthesis of 2-aryl-glycals and their elaboration to 2-C-aryl-alpha-glycosides and 1,5-anhydro-2-C-ary1-2-deoxy alditols are described. The use of reliable, efficient phosphine-free Suzuki-Miyaura cross-coupling of 2-iodoglycals in aqueous media as a key step proceeds with complete regioselectivity at C-2 and enables access to 2-aryl-glycals with different configurations in excellent yields.

  • Others:

    Link to the original source: https://pubs.acs.org/doi/10.1021/ol3003139
    APA: Cobo, Isidro; Matheu, M Isabel; Castillon, Sergio; Boutureira, Omar; Davis, Benjamin G (2012). Phosphine-Free Suzuki-Miyaura Cross-Coupling in Aqueous Media Enables Access to 2-C-Aryl-Glycosides. Organic Letters, 14(7), 1728-1731. DOI: 10.1021/ol3003139
    Paper original source: Organic Letters. 14 (7): 1728-1731
    Article's DOI: 10.1021/ol3003139
    Journal publication year: 2012
    Entity: Universitat Rovira i Virgili
    Paper version: info:eu-repo/semantics/acceptedVersion
    Record's date: 2025-01-08
    URV's Author/s: Boutureira Martín, Omar / Castillón Miranda, Sergio / Matheu Malpartida, María Isabel
    Department: Química Analítica i Química Orgànica
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Publication Type: Journal Publications
    Author, as appears in the article.: Cobo, Isidro; Matheu, M Isabel; Castillon, Sergio; Boutureira, Omar; Davis, Benjamin G
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Thematic Areas: Química, Physical and theoretical chemistry, Organic chemistry, Medicina ii, Medicina i, Materiais, Interdisciplinar, General medicine, Farmacia, Ciências biológicas ii, Ciências biológicas i, Ciências agrárias i, Chemistry, organic, Biotecnología, Biodiversidade, Biochemistry
    Author's mail: omar.boutureira@urv.cat, maribel.matheu@urv.cat, sergio.castillon@urv.cat

  • Keywords:

    Water
    Stereoselective-synthesis
    Phosphines
    Phosphine
    Peracetylated glycals
    Organic-synthesis
    Molecular structure
    Glycosyltransferase inhibitors
    Glycosides
    Glycals
    Exo-glycals
    Efficient synthesis
    Cross-coupling
    Catalysis
    Carbohydrate-chemistry
    C-glycoside synthesis
    Arylboronic acids
    Aryl glycosides
    Biochemistry
    Chemistry
    Organic
    Organic Chemistry
    Physical and Theoretical Chemistry
    Química
    Medicina ii
    Medicina i
    Materiais
    Interdisciplinar
    General medicine
    Farmacia
    Ciências biológicas ii
    Ciências biológicas i
    Ciências agrárias i
    Biotecnología
    Biodiversidade

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