Articles producció científica> Química Física i Inorgànica

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

  • Dades identificatives

    Identificador: imarina:5133298
    Handle: https://hdl.handle.net/20.500.11797/imarina5133298
    Autors:
    Maza RJ, Davenport E, Miralles N, Carbó JJ, Fernández E
    Resum:
    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.

  • Altres:

    Autor segons l'article: Maza RJ, Davenport E, Miralles N, Carbó JJ, Fernández E
    Departament: Química Física i Inorgànica
    Autor/s de la URV: Carbó Martin, Jorge Juan / Fernández Gutiérrez, Maria Elena / MIRALLES PRAT, NURIA
    Paraules clau: Hydroboration Diboration Conjugated dienes Catalyzed 1,4-hydroboration Aldehydes 1,4-diboration
    Resum: 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.
    Àrees temàtiques: 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
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 15237060
    Adreça de correu electrònic de l'autor: mariaelena.fernandez@urv.cat j.carbo@urv.cat
    Identificador de l'autor: 0000-0001-9025-1791 0000-0002-3945-6721
    Data d'alta del registre: 2023-02-26
    Versió de l'article dipositat: info:eu-repo/semantics/acceptedVersion
    Enllaç font original: https://pubs.acs.org/doi/10.1021/acs.orglett.9b00531
    Referència a l'article segons font original: Organic Letters. 21 (7): 2251-2255
    Referència de l'ítem segons les normes 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
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    DOI de l'article: 10.1021/acs.orglett.9b00531
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2019
    Tipus de publicació: Journal Publications

  • Paraules clau:

    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

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