Articles producció científica> Química Física i Inorgànica

Synthesis and reactivity of 1,1-diborylalkanes towards C-C bond formation and related mechanisms

  • Datos identificativos

    Identificador: imarina:5132814
    Autores:
    Miralles, NuriaMaza, Ricardo J.Fernandez, Elena
    Resumen:
    gem‐Diborylalkanes have emerged as efficient reagents for synthesizing organoboron compounds through selective C−C bond‐forming reactions. Activation of the 1,1‐diborylalkanes generates carbanions with enhanced stability that are able to react with a series of electrophiles, carbonyl compounds, imines and epoxides to promote formation of a new C−C bond. These new sets of reactions have become general for a wide range of substrates and they can be understood by alternative mechanisms that justify the potential use of these reagents. The formation of C-C(B) bonds can be achieved with chemo‐, diastereo‐ and enantioselectivity, because the nucleophilc α‐boryl or α‐diboryl carbanions attack in a stereoselective manner, by means of the catalyst involved. The synthesis of gem‐diborylalkanes has also been promoted by innovative methods and facilitates access to multiborylated reagents with different substituents and properties.
  • Otros:

    Autor según el artículo: Miralles, Nuria; Maza, Ricardo J.; Fernandez, Elena;
    Departamento: Química Física i Inorgànica
    Autor/es de la URV: Fernández Gutiérrez, Maria Elena / MIRALLES PRAT, NURIA
    Palabras clave: Mechanism Diborylmethane Cross-coupling Borylmethylation 1,1-diborylalkanes
    Resumen: gem‐Diborylalkanes have emerged as efficient reagents for synthesizing organoboron compounds through selective C−C bond‐forming reactions. Activation of the 1,1‐diborylalkanes generates carbanions with enhanced stability that are able to react with a series of electrophiles, carbonyl compounds, imines and epoxides to promote formation of a new C−C bond. These new sets of reactions have become general for a wide range of substrates and they can be understood by alternative mechanisms that justify the potential use of these reagents. The formation of C-C(B) bonds can be achieved with chemo‐, diastereo‐ and enantioselectivity, because the nucleophilc α‐boryl or α‐diboryl carbanions attack in a stereoselective manner, by means of the catalyst involved. The synthesis of gem‐diborylalkanes has also been promoted by innovative methods and facilitates access to multiborylated reagents with different substituents and properties.
    Áreas temáticas: Química Organic chemistry Materiais Engenharias iv Engenharias ii Ciências biológicas ii Ciência de alimentos Chemistry, organic Chemistry, applied Catalysis Biodiversidade Astronomia / física
    Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 16154150
    Direcció de correo del autor: mariaelena.fernandez@urv.cat
    Identificador del autor: 0000-0001-9025-1791
    Fecha de alta del registro: 2024-09-07
    Versión del articulo depositado: info:eu-repo/semantics/acceptedVersion
    Enlace a la fuente original: https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.201701390
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referencia al articulo segun fuente origial: Advanced Synthesis & Catalysis. 360 (7): 1306-1327
    Referencia de l'ítem segons les normes APA: Miralles, Nuria; Maza, Ricardo J.; Fernandez, Elena; (2018). Synthesis and reactivity of 1,1-diborylalkanes towards C-C bond formation and related mechanisms. Advanced Synthesis & Catalysis, 360(7), 1306-1327. DOI: 10.1002/adsc.201701390
    DOI del artículo: 10.1002/adsc.201701390
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2018
    Tipo de publicación: Journal Publications
  • Palabras clave:

    Catalysis,Chemistry, Applied,Chemistry, Organic,Organic Chemistry
    Mechanism
    Diborylmethane
    Cross-coupling
    Borylmethylation
    1,1-diborylalkanes
    Química
    Organic chemistry
    Materiais
    Engenharias iv
    Engenharias ii
    Ciências biológicas ii
    Ciência de alimentos
    Chemistry, organic
    Chemistry, applied
    Catalysis
    Biodiversidade
    Astronomia / física
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