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

  • Dades identificatives

    Identificador: imarina:9246126
    Autors:
    Li XVillar-Yanez ANgassam Tounzoua CBenet-Buchholz JGrignard BBo CDetrembleur CKleij AW
    Resum:
    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.
  • Altres:

    Autor segons l'article: Li X; Villar-Yanez A; Ngassam Tounzoua C; Benet-Buchholz J; Grignard B; Bo C; Detrembleur C; Kleij AW
    Departament: Química Física i Inorgànica
    Autor/s de la URV: Benet Buchholz, Jordi / Bo Jané, Carles / Villar Yanez, Alba
    Paraules clau: 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
    Resum: 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.
    Àrees temàtiques: Química Materiais Interdisciplinar General chemistry Engenharias ii Ciências agrárias i Chemistry, physical Chemistry (miscellaneous) Chemistry (all) Catalysis Astronomia / física
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    Adreça de correu electrònic de l'autor: carles.bo@urv.cat alba.villar@estudiants.urv.cat
    Identificador de l'autor: 0000-0001-9581-2922
    Data d'alta del registre: 2024-09-07
    Versió de l'article dipositat: info:eu-repo/semantics/publishedVersion
    Enllaç font original: https://pubs.acs.org/doi/10.1021/acscatal.1c05773
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referència a l'article segons font original: Acs Catalysis. 12 (5): 2854-2860
    Referència 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 de l'article: 10.1021/acscatal.1c05773
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2022
    Tipus de publicació: Journal Publications
  • Paraules clau:

    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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