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, I; Matheu, MI; Castillón, S; Boutureira, O; Davis, BG
    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, I; Matheu, MI; Castillón, S; Boutureira, O; Davis, BG (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: 2012-04-06
    Entity: Universitat Rovira i Virgili
    Paper version: info:eu-repo/semantics/acceptedVersion
    Record's date: 2026-05-09
    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, I; Matheu, MI; Castillón, S; Boutureira, O; Davis, BG
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Thematic Areas: Physical and theoretical chemistry, Organic chemistry, General medicine, Chemistry, organic, Biotecnología, Biodiversidade, Biochemistry
    Author's mail: sergio.castillon@urv.cat, sergio.castillon@urv.cat, omar.boutureira@urv.cat, omar.boutureira@urv.cat, maribel.matheu@urv.cat, maribel.matheu@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
    General medicine
    Biotecnología
    Biodiversidade

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