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Cascade Transformation of Carbon Dioxide and Alkyne-1, n-diols into Densely Substituted Cyclic Carbonates

  • Datos identificativos

    Identificador: imarina:9246126
    Autores:
    Li XVillar-Yanez ANgassam Tounzoua CBenet-Buchholz JGrignard BBo CDetrembleur CKleij AW
    Resumen:
    A silver-catalyzed cascade conversion of modular alkyne-1,n-diols and carbon dioxide has been developed allowing for the selective formation of keto-functionalized cyclic carbonates. The protocol is characterized by its operational simplicity, excellent scope of carbonate-based heterocycles, and mild reaction conditions. In situ IR studies, control experiments, and detailed computational analysis of these manifolds reveal the intermediacy of an α-alkylidene carbonate that is intercepted by an intramolecular alcohol nucleophile. The synthetic potential of this conceptually attractive CO2 transformation is demonstrated in the preparation of larger ring carbonates and their thermal rearrangement to sterically crowded, five-membered fused carbonate products.
  • Otros:

    Autor según el artículo: Li X; Villar-Yanez A; Ngassam Tounzoua C; Benet-Buchholz J; Grignard B; Bo C; Detrembleur C; Kleij AW
    Departamento: Química Física i Inorgànica
    Autor/es de la URV: Benet Buchholz, Jordi / Bo Jané, Carles / Villar Yanez, Alba
    Palabras clave: Ring-opening polymerization Homogeneous catalysis Heterocycles Cascade reactions Carbon dioxide Alkyne-1,n-diols Alkyne-1, n-diols rearrangement propargylic alcohols homogeneous catalysis heterocycles epoxides diols conversion co2 chemicals catalytic strategies cascade reactions carbon dioxide atmospheric-pressure
    Resumen: A silver-catalyzed cascade conversion of modular alkyne-1,n-diols and carbon dioxide has been developed allowing for the selective formation of keto-functionalized cyclic carbonates. The protocol is characterized by its operational simplicity, excellent scope of carbonate-based heterocycles, and mild reaction conditions. In situ IR studies, control experiments, and detailed computational analysis of these manifolds reveal the intermediacy of an α-alkylidene carbonate that is intercepted by an intramolecular alcohol nucleophile. The synthetic potential of this conceptually attractive CO2 transformation is demonstrated in the preparation of larger ring carbonates and their thermal rearrangement to sterically crowded, five-membered fused carbonate products.
    Áreas temáticas: Química Materiais Interdisciplinar General chemistry Engenharias ii Ciências agrárias i Chemistry, physical Chemistry (miscellaneous) Chemistry (all) Catalysis Astronomia / física
    Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
    Direcció de correo del autor: carles.bo@urv.cat alba.villar@estudiants.urv.cat
    Identificador del autor: 0000-0001-9581-2922
    Fecha de alta del registro: 2024-09-07
    Versión del articulo depositado: info:eu-repo/semantics/publishedVersion
    Enlace a la fuente original: https://pubs.acs.org/doi/10.1021/acscatal.1c05773
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referencia al articulo segun fuente origial: Acs Catalysis. 12 (5): 2854-2860
    Referencia de l'ítem segons les normes APA: Li X; Villar-Yanez A; Ngassam Tounzoua C; Benet-Buchholz J; Grignard B; Bo C; Detrembleur C; Kleij AW (2022). Cascade Transformation of Carbon Dioxide and Alkyne-1, n-diols into Densely Substituted Cyclic Carbonates. Acs Catalysis, 12(5), 2854-2860. DOI: 10.1021/acscatal.1c05773
    DOI del artículo: 10.1021/acscatal.1c05773
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2022
    Tipo de publicación: Journal Publications
  • Palabras clave:

    Catalysis,Chemistry (Miscellaneous),Chemistry, Physical
    Ring-opening polymerization
    Homogeneous catalysis
    Heterocycles
    Cascade reactions
    Carbon dioxide
    Alkyne-1,n-diols
    Alkyne-1, n-diols
    rearrangement
    propargylic alcohols
    homogeneous catalysis
    heterocycles
    epoxides
    diols
    conversion
    co2
    chemicals
    catalytic strategies
    cascade reactions
    carbon dioxide
    atmospheric-pressure
    Química
    Materiais
    Interdisciplinar
    General chemistry
    Engenharias ii
    Ciências agrárias i
    Chemistry, physical
    Chemistry (miscellaneous)
    Chemistry (all)
    Catalysis
    Astronomia / física
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