Articles producció científica> Química Física i Inorgànica

Transition-Metal-Free Allylic Borylation of 1,3-Dienes

  • Identification data

    Identifier: imarina:5133298
    Handle: https://hdl.handle.net/20.500.11797/imarina5133298
    Authors:
    Maza RJ, Davenport E, Miralles N, Carbó JJ, Fernández E
    Abstract:
    This work explains the reactivity of diboron reagents with 1,3-dienes in a transition-metal-free context. The sole addition of Na2CO3 (30 mol %) to bis(pinacolato)diboron in MeOH allows the 1,4-hydroboration of cyclic and noncyclic 1,3-dienes. The electronic influence on the substrate guarantees the conjugated 1,4-hydroboration versus 1,2-diboration. DFT calculations show that the distribution of charge in the allylic anion intermediate governs the selectivity toward 1,4-hydroboration, while the favored trans configuration in diene reagents determines the preference for the E allyl boronate products.

  • Others:

    Author, as appears in the article.: Maza RJ, Davenport E, Miralles N, Carbó JJ, Fernández E
    Department: Química Física i Inorgànica
    URV's Author/s: Carbó Martin, Jorge Juan / Fernández Gutiérrez, Maria Elena / MIRALLES PRAT, NURIA
    Keywords: Hydroboration Diboration Conjugated dienes Catalyzed 1,4-hydroboration Aldehydes 1,4-diboration
    Abstract: This work explains the reactivity of diboron reagents with 1,3-dienes in a transition-metal-free context. The sole addition of Na2CO3 (30 mol %) to bis(pinacolato)diboron in MeOH allows the 1,4-hydroboration of cyclic and noncyclic 1,3-dienes. The electronic influence on the substrate guarantees the conjugated 1,4-hydroboration versus 1,2-diboration. DFT calculations show that the distribution of charge in the allylic anion intermediate governs the selectivity toward 1,4-hydroboration, while the favored trans configuration in diene reagents determines the preference for the E allyl boronate products.
    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
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 15237060
    Author's mail: mariaelena.fernandez@urv.cat j.carbo@urv.cat
    Author identifier: 0000-0001-9025-1791 0000-0002-3945-6721
    Record's date: 2023-02-26
    Papper version: info:eu-repo/semantics/acceptedVersion
    Link to the original source: https://pubs.acs.org/doi/10.1021/acs.orglett.9b00531
    Papper original source: Organic Letters. 21 (7): 2251-2255
    APA: Maza RJ, Davenport E, Miralles N, Carbó JJ, Fernández E (2019). Transition-Metal-Free Allylic Borylation of 1,3-Dienes. Organic Letters, 21(7), 2251-2255. DOI: 10.1021/acs.orglett.9b00531
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Article's DOI: 10.1021/acs.orglett.9b00531
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2019
    Publication Type: Journal Publications

  • Keywords:

    Biochemistry,Chemistry, Organic,Organic Chemistry,Physical and Theoretical Chemistry
    Hydroboration
    Diboration
    Conjugated dienes
    Catalyzed 1,4-hydroboration
    Aldehydes
    1,4-diboration
    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

  • Documents:

    DocumentPrincipal

  • Cerca a google

    Search to google scholar