Articles producció científica> Química Física i Inorgànica

Boron-Copper 1,3-Rearrangement: the New Concept Behind the Boryl Migration from C(sp2) in Alkenyl Boranes to C(sp3)

  • Identification data

    Identifier: imarina:9322008
  • Authors:

    Dominguez-Molano, P
    Weeks, R
    Maza, RJ
    Carbó, JJ
    Fernández, E
  • Others:

    Author, as appears in the article.: Dominguez-Molano, P; Weeks, R; Maza, RJ; Carbó, JJ; Fernández, E
    Department: Química Física i Inorgànica
    URV's Author/s: Carbó Martin, Jorge Juan / Domínguez Molano, Paula / Fernández Gutiérrez, Maria Elena / Maza Quiroga, Ricardo José
    Keywords: Mechanism Dft calculations Copper Boryl-migration Alkylidenecyclobutanes
    Abstract: Regioselective borylcupration of borylated skipped (Z)-dienes generates diborylated alkylcopper species that are involved in an intramolecular stereospecific B/Cu 1,3-rearrangement by migration of Bpin moiety from C(sp2) to C(sp3). DFT mechanistic studies showed that boryl migration occurs through the formation of 4-membered boracycle intermediate with a moderate free-energy barrier. Moreover, the use of KOMe forms stable Lewis base adducts with Bpin moieties that blocks the reaction. Subsequently to the 1,3-boron shift, the in situ electrophilic trapping allows selective C−H, C−C and C−X bonds, followed by intramolecular cross coupling giving access to cyclic functionalized alkylidenecyclohexanes or alkylidenecyclobutanes.
    Thematic Areas: Química Medicina ii Medicina i Materiais Interdisciplinar General medicine General chemistry Farmacia Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Astronomia / física
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Author's mail: paula.dominguez@urv.cat mariaelena.fernandez@urv.cat j.carbo@urv.cat ricardojose.maza@estudiants.urv.cat ricardojose.maza@estudiants.urv.cat paula.dominguez@urv.cat
    Author identifier: 0000-0001-9025-1791 0000-0002-3945-6721
    Record's date: 2024-01-13
    Papper version: info:eu-repo/semantics/publishedVersion
    Link to the original source: https://onlinelibrary.wiley.com/doi/full/10.1002/anie.202304791
    Licence document URL: http://repositori.urv.cat/ca/proteccio-de-dades/
    Papper original source: Angewandte Chemie (International Ed. Print). 62 (30): e202304791-
    APA: Dominguez-Molano, P; Weeks, R; Maza, RJ; Carbó, JJ; Fernández, E (2023). Boron-Copper 1,3-Rearrangement: the New Concept Behind the Boryl Migration from C(sp2) in Alkenyl Boranes to C(sp3). Angewandte Chemie (International Ed. Print), 62(30), e202304791-. DOI: 10.1002/anie.202304791
    Article's DOI: 10.1002/anie.202304791
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2023
    Publication Type: Journal Publications
  • Keywords:

    Catalysis,Chemistry,Chemistry (Miscellaneous),Chemistry, Multidisciplinary
    Mechanism
    Dft calculations
    Copper
    Boryl-migration
    Alkylidenecyclobutanes
    Química
    Medicina ii
    Medicina i
    Materiais
    Interdisciplinar
    General medicine
    General chemistry
    Farmacia
    Engenharias ii
    Ciências biológicas iii
    Ciências biológicas ii
    Ciências biológicas i
    Chemistry, multidisciplinary
    Chemistry (miscellaneous)
    Chemistry (all)
    Chemistry
    Catalysis
    Astronomia / física
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