Articles producció científica> Química Física i Inorgànica

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

  • Datos identificativos

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

  • Otros:

    Autor según el artículo: Maza RJ, Davenport E, Miralles N, Carbó JJ, Fernández E
    Departamento: Química Física i Inorgànica
    Autor/es de la URV: Carbó Martin, Jorge Juan / Fernández Gutiérrez, Maria Elena / MIRALLES PRAT, NURIA
    Palabras clave: Hydroboration Diboration Conjugated dienes Catalyzed 1,4-hydroboration Aldehydes 1,4-diboration
    Resumen: 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.
    Áreas temáticas: 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
    Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 15237060
    Direcció de correo del autor: mariaelena.fernandez@urv.cat j.carbo@urv.cat
    Identificador del autor: 0000-0001-9025-1791 0000-0002-3945-6721
    Fecha de alta del registro: 2023-02-26
    Versión del articulo depositado: info:eu-repo/semantics/acceptedVersion
    Enlace a la fuente original: https://pubs.acs.org/doi/10.1021/acs.orglett.9b00531
    Referencia al articulo segun fuente origial: Organic Letters. 21 (7): 2251-2255
    Referencia 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 Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    DOI del artículo: 10.1021/acs.orglett.9b00531
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2019
    Tipo de publicación: Journal Publications

  • Palabras clave:

    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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