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Assembly of Complex 1,4-Cycloheptadienes by (4+3) Cycloaddition of Rhodium(II) and Gold(I) Non-Acceptor Carbenes

  • Identification data

    Identifier: imarina:9093095
    Authors:
    Armengol-Relats, HelenaMato, MauroEchavarren, Antonio M.
    Abstract:
    The formal (4+3) cycloaddition of 1,3-dienes with Rh(II) and Au(I) non-acceptor vinyl carbenes, generated from vinylcycloheptatrienes or alkoxyenynes, respectively, leads to 1,4-cycloheptadienes featuring complex and diverse substitution patterns, including natural dyctiopterene C ' and a hydroxylated derivative of carota-1,4-diene. A complete mechanistic picture is presented, in which Au(I) and Rh(II) non-acceptor vinyl carbenes were shown to undergo a vinylcyclopropanation/Cope rearrangement or a direct (4+3) cycloaddition that takes place in a non-concerted manner.
  • Others:

    Author, as appears in the article.: Armengol-Relats, Helena; Mato, Mauro; Echavarren, Antonio M.;
    Department: Química Analítica i Química Orgànica
    e-ISSN: 1521-3757
    URV's Author/s: Armengol Relats, Helena / ECHAVARREN PABLOS, ANTONIO / Mato Gómez, Mauro
    Keywords: Retro-buchner reaction Metal carbenes Hydrocarbons H functionalization Enyne cycloisomerizations Dienediynes Decarbenation reactions Cyclopropanes Cyclopropanation/cope rearrangement Cycloheptadienes Cycloadditions Cyclization Construction Catalyzed cycloisomerization Access
    Abstract: The formal (4+3) cycloaddition of 1,3-dienes with Rh(II) and Au(I) non-acceptor vinyl carbenes, generated from vinylcycloheptatrienes or alkoxyenynes, respectively, leads to 1,4-cycloheptadienes featuring complex and diverse substitution patterns, including natural dyctiopterene C ' and a hydroxylated derivative of carota-1,4-diene. A complete mechanistic picture is presented, in which Au(I) and Rh(II) non-acceptor vinyl carbenes were shown to undergo a vinylcyclopropanation/Cope rearrangement or a direct (4+3) cycloaddition that takes place in a non-concerted manner.
    Thematic Areas: Química Medicina ii Medicina i Materiais Interdisciplinar General medicine General chemistry Farmacia Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Astronomia / física
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 0044-8249
    Author's mail: antoniomaria.echavarren@urv.cat helena.armengol@estudiants.urv.cat
    Author identifier: 0000-0002-6418-7930
    Record's date: 2024-07-27
    Papper version: info:eu-repo/semantics/publishedVersion
    Link to the original source: https://onlinelibrary.wiley.com/doi/full/10.1002/anie.202012092
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Papper original source: Angewandte Chemie (International Ed. Print). 60 (4): 1916-1922
    APA: Armengol-Relats, Helena; Mato, Mauro; Echavarren, Antonio M.; (2021). Assembly of Complex 1,4-Cycloheptadienes by (4+3) Cycloaddition of Rhodium(II) and Gold(I) Non-Acceptor Carbenes. Angewandte Chemie (International Ed. Print), 60(4), 1916-1922. DOI: 10.1002/anie.202012092
    Article's DOI: 10.1002/anie.202012092
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2021
    Publication Type: Journal Publications
  • Keywords:

    Catalysis,Chemistry,Chemistry (Miscellaneous),Chemistry, Multidisciplinary
    Retro-buchner reaction
    Metal carbenes
    Hydrocarbons
    H functionalization
    Enyne cycloisomerizations
    Dienediynes
    Decarbenation reactions
    Cyclopropanes
    Cyclopropanation/cope rearrangement
    Cycloheptadienes
    Cycloadditions
    Cyclization
    Construction
    Catalyzed cycloisomerization
    Access
    Química
    Medicina ii
    Medicina i
    Materiais
    Interdisciplinar
    General medicine
    General chemistry
    Farmacia
    Engenharias ii
    Ciências biológicas iii
    Ciências biológicas ii
    Ciências biológicas i
    Chemistry, multidisciplinary
    Chemistry (miscellaneous)
    Chemistry (all)
    Chemistry
    Catalysis
    Astronomia / física
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