Articles producció científicaQuímica Física i Inorgànica

Transition-Metal-Free Allylic Borylation of 1

  • Identification data

    Identifier:  imarina:5133298
    Handle: https://hdl.handle.net/20.500.11797/imarina5133298
    Authors:  Maza, Ricardo J; Davenport, Elliot; Miralles, Nuria; Carbo, Jorge J; Fernandez, Elena
    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:

    Link to the original source: https://pubs.acs.org/doi/10.1021/acs.orglett.9b00531
    APA: Maza, Ricardo J; Davenport, Elliot; Miralles, Nuria; Carbo, Jorge J; Fernandez, Elena (2019). Transition-Metal-Free Allylic Borylation of 1,3-Dienes. Organic Letters, 21(7), 2251-2255. DOI: 10.1021/acs.orglett.9b00531
    Paper original source: Organic Letters. 21 (7): 2251-2255
    Article's DOI: 10.1021/acs.orglett.9b00531
    Journal publication year: 2019
    Entity: Universitat Rovira i Virgili
    Paper version: info:eu-repo/semantics/acceptedVersion
    Record's date: 2025-02-18
    URV's Author/s: Carbó Martin, Jorge Juan / Fernández Gutiérrez, Maria Elena / MIRALLES PRAT, NURIA
    Department: Química Física i Inorgànica
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Publication Type: Journal Publications
    ISSN: 15237060
    Author, as appears in the article.: Maza, Ricardo J; Davenport, Elliot; Miralles, Nuria; Carbo, Jorge J; Fernandez, Elena
    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: j.carbo@urv.cat, mariaelena.fernandez@urv.cat

  • Keywords:

    Hydroboration
    Diboration
    Conjugated dienes
    Catalyzed 1
    4-hydroboration
    Aldehydes
    4-diboration
    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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