Articles producció científica> Química Analítica i Química Orgànica

High-Yield Synthesis of a Long-Sought, Labile Ru-NHC Complex and Its Application to the Concise Synthesis of Second-Generation Olefin Metathesis Catalysts

  • Datos identificativos

    Identificador: imarina:9149602
    Handle: http://hdl.handle.net/20.500.11797/imarina9149602
  • Autores:

    Day, Craig S.
    Fogg, Deryn E.
  • Otros:

    Autor según el artículo: Day, Craig S.; Fogg, Deryn E.;
    Departamento: Química Analítica i Química Orgànica
    Autor/es de la URV: Day, Craig
    Palabras clave: Acceptor properties Acrylate metathesis Chemical-shifts Decomposition Hydrogenation Ligands synthesis N-heterocyclic carbenes Polymerization Ring-closing metathesis Ruthenium complexes
    Resumen: The controlled reaction of [RuCl2(p-cymene)](2) with H(2)IMes generates the previously challenging precatalyst and Ru synthon RuCl2(p-cymene)(H(2)IMes) (Ru-2) in 96% isolated yield. Critical to success is inhibiting premature p-cymene displacement. This is achieved by carrying out the synthesis at ambient temperatures, protected from light, and at sufficient dilutions (25 mM in THF) to enable stoichiometric control and inhibit bimolecular decomposition. The ease with which p-cymene loss can be deliberately induced, however, is key to the utility of Ru-2 in both catalysis and catalyst synthesis. The transformation of Ru-2 into two second-generation olefin metathesis catalysts is described. RuCl2(H(2)IMes)(=CH(o-C6H4-(OPr)-Pr-i)) (HII) and RuCl2(H(2)IMes)(PPh3)(=CHPh) GII' (a desirable, faster-initiating analogue of GII) are accessible in ca. 80% yield over two steps from commercially available [RuCl2(p-cymene)](2). Synthesis from RuCl2(PPh3)(3), in comparison, requires three or four steps for HII or GII', respectively, and proceeds in lower yields.
    Áreas temáticas: Astronomia / física Chemistry, inorganic & nuclear Chemistry, organic Ciências agrárias i Ciências biológicas ii Engenharias ii Inorganic chemistry Materiais Organic chemistry Physical and theoretical chemistry Química
    Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
    Direcció de correo del autor: craig.day@estudiants.urv.cat
    Identificador del autor: 0000-0002-6931-0280
    Fecha de alta del registro: 2021-10-10
    Página final: 4555
    Volumen de revista: 37
    Versión del articulo depositado: info:eu-repo/semantics/publishedVersion
    Enlace a la fuente original: https://pubs.acs.org/doi/10.1021/acs.organomet.8b00745
    Referencia al articulo segun fuente origial: Organometallics. 37 (24): 4551-4555
    Referencia de l'ítem segons les normes APA: Day, Craig S.; Fogg, Deryn E.; (2018). High-Yield Synthesis of a Long-Sought, Labile Ru-NHC Complex and Its Application to the Concise Synthesis of Second-Generation Olefin Metathesis Catalysts. Organometallics, 37(24), 4551-4555. DOI: 10.1021/acs.organomet.8b00745
    URL Documento de licencia: http://repositori.urv.cat/ca/proteccio-de-dades/
    DOI del artículo: 10.1021/acs.organomet.8b00745
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2018
    Página inicial: 4551
    Tipo de publicación: Journal Publications
  • Palabras clave:

    Chemistry, Inorganic & Nuclear,Chemistry, Organic,Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry
    Acceptor properties
    Acrylate metathesis
    Chemical-shifts
    Decomposition
    Hydrogenation
    Ligands synthesis
    N-heterocyclic carbenes
    Polymerization
    Ring-closing metathesis
    Ruthenium complexes
    Astronomia / física
    Chemistry, inorganic & nuclear
    Chemistry, organic
    Ciências agrárias i
    Ciências biológicas ii
    Engenharias ii
    Inorganic chemistry
    Materiais
    Organic chemistry
    Physical and theoretical chemistry
    Química
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