Articles producció científica> Química Física i Inorgànica

Filling the Gaps in the Challenging Asymmetric Hydrogenation of Exocyclic Benzofused Alkenes with Ir-P,N Catalysts

  • Datos identificativos

    Identificador: imarina:9283365
    Autores:
    Biosca, Mariade la Cruz-Sanchez, PolTarr, DanielLlanes, PatriciaKarlsson, Erik A.Margalef, JessicaPamies, OscarPericas, Miquel A.Dieguez, Montserrat
    Resumen:
    Herein, we report a chiral phosphine-triazole ligand for the Ir-catalyzed asymmetric hydrogenation of exocyclic benzofused alkenes. Overcoming previous limitations, the catalytic system is able to successfully hydrogenate exocyclic olefins bearing a benzofused five- and six-membered ring motif (ee's between 92 to 99%). The catalyst tolerates well the presence of several substituents and substitution patterns at both aromatic rings. The absence of a competing isomerization process together with the perfect fit of the olefins in the catalyst chiral pocket are key to surpass the previous limitations in the hydrogenation of both 5- and 6-membered ring benzofused exocyclic olefins.
  • Otros:

    Autor según el artículo: Biosca, Maria; de la Cruz-Sanchez, Pol; Tarr, Daniel; Llanes, Patricia; Karlsson, Erik A.; Margalef, Jessica; Pamies, Oscar; Pericas, Miquel A.; Dieguez, Montserrat;
    Departamento: Química Física i Inorgànica
    Autor/es de la URV: Biosca Brull, Maria / De La Cruz Sánchez Badia, Pol / Diéguez Fernández, Montserrat / Margalef Pallarès, Jèssica / Pamies Ollé, Oscar / Tarr González, Daniel James
    Código de proyecto: Grant agreement No. 945413
    Palabras clave: Versatile P,n-ligands P N-ligands Molecular-orbital methods Minimally functionalized olefins Mechanistic insights Ligands Iridium Highly enantioselective hydrogenation Exocyclic olefins Effective core potentials Dft calculations Deuterogenation Basis-sets Atoms Asymmetric hydrogenation
    Resumen: Herein, we report a chiral phosphine-triazole ligand for the Ir-catalyzed asymmetric hydrogenation of exocyclic benzofused alkenes. Overcoming previous limitations, the catalytic system is able to successfully hydrogenate exocyclic olefins bearing a benzofused five- and six-membered ring motif (ee's between 92 to 99%). The catalyst tolerates well the presence of several substituents and substitution patterns at both aromatic rings. The absence of a competing isomerization process together with the perfect fit of the olefins in the catalyst chiral pocket are key to surpass the previous limitations in the hydrogenation of both 5- and 6-membered ring benzofused exocyclic olefins.
    Áreas temáticas: Química Organic chemistry Materiais Engenharias iv Engenharias ii Ciências biológicas ii Ciência de alimentos Chemistry, organic Chemistry, applied Catalysis Biodiversidade Astronomia / física
    Direcció de correo del autor: danieljames.tarr@urv.cat maria.biosca@urv.cat pol.delacruzsanchez@estudiants.urv.cat pol.delacruzsanchez@estudiants.urv.cat oscar.pamies@urv.cat montserrat.dieguez@urv.cat
    Identificador del autor: 0000-0002-9116-6318 0000-0002-2352-8508 0000-0002-8450-0656
    Fecha de alta del registro: 2024-08-03
    Versión del articulo depositado: info:eu-repo/semantics/publishedVersion
    Enlace a la fuente original: https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202200870
    Programa de financiación: Marie Skłodowska-Curie Actions - European Union's Horizon 2020 research and innovation programme
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referencia al articulo segun fuente origial: Advanced Synthesis & Catalysis. 365 (2): 167-177
    Referencia de l'ítem segons les normes APA: Biosca, Maria; de la Cruz-Sanchez, Pol; Tarr, Daniel; Llanes, Patricia; Karlsson, Erik A.; Margalef, Jessica; Pamies, Oscar; Pericas, Miquel A.; Diegu (2023). Filling the Gaps in the Challenging Asymmetric Hydrogenation of Exocyclic Benzofused Alkenes with Ir-P,N Catalysts. Advanced Synthesis & Catalysis, 365(2), 167-177. DOI: 10.1002/adsc.202200870
    Acrónimo: MFP-Plus
    DOI del artículo: 10.1002/adsc.202200870
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2023
    Acción del progama de financiación: Martí i Franquès COFUND Doctoral Programme
    Tipo de publicación: Journal Publications
  • Palabras clave:

    Catalysis,Chemistry, Applied,Chemistry, Organic,Organic Chemistry
    Versatile
    P,n-ligands
    P
    N-ligands
    Molecular-orbital methods
    Minimally functionalized olefins
    Mechanistic insights
    Ligands
    Iridium
    Highly enantioselective hydrogenation
    Exocyclic olefins
    Effective core potentials
    Dft calculations
    Deuterogenation
    Basis-sets
    Atoms
    Asymmetric hydrogenation
    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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