Articles producció científica> Química Física i Inorgànica

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

  • Identification data

    Identifier: imarina:9246126
    Authors:
    Li XVillar-Yanez ANgassam Tounzoua CBenet-Buchholz JGrignard BBo CDetrembleur CKleij AW
    Abstract:
    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.
  • Others:

    Author, as appears in the article.: Li X; Villar-Yanez A; Ngassam Tounzoua C; Benet-Buchholz J; Grignard B; Bo C; Detrembleur C; Kleij AW
    Department: Química Física i Inorgànica
    URV's Author/s: Benet Buchholz, Jordi / Bo Jané, Carles / Villar Yanez, Alba
    Keywords: 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
    Abstract: 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.
    Thematic Areas: Química Materiais Interdisciplinar General chemistry Engenharias ii Ciências agrárias i Chemistry, physical Chemistry (miscellaneous) Chemistry (all) Catalysis Astronomia / física
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Author's mail: carles.bo@urv.cat alba.villar@estudiants.urv.cat
    Author identifier: 0000-0001-9581-2922
    Record's date: 2024-09-07
    Papper version: info:eu-repo/semantics/publishedVersion
    Link to the original source: https://pubs.acs.org/doi/10.1021/acscatal.1c05773
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Papper original source: Acs Catalysis. 12 (5): 2854-2860
    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
    Article's DOI: 10.1021/acscatal.1c05773
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2022
    Publication Type: Journal Publications
  • Keywords:

    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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