Articles producció científica> Química Analítica i Química Orgànica

Silver-Free Au(I) Catalysis Enabled by Bifunctional Urea- and Squaramide-Phosphine Ligands via H-Bonding

  • Datos identificativos

    Identificador: imarina:9221756
    Autores:
    Franchino, AllegraMarti, AlexNejrotti, StefanoEchavarren, Antonio M.
    Resumen:
    A library of gold(I) chloride complexes with phosphine ligands incorporating pendant (thio)urea and squaramide H-bond donors was prepared with the aim of promoting chloride abstraction from Au(I) via H-bonding. In the absence of silver additives, complexes bearing squaramides and trifluoromethylated aromatic ureas displayed good catalytic activity in the cyclization of N-propargyl benzamides, as well as in a 1,6-enyne cycloisomerization, a tandem cyclization-indole addition reaction and the hydrohydrazination of phenylacetylene. Kinetic studies and DFT calculations indicate that the energetic span of the reaction is accounted by both the chloride abstraction step, facilitated by the bidentate H-bond donor via an associative mechanism, and the subsequent cyclization step.
  • Otros:

    Autor según el artículo: Franchino, Allegra; Marti, Alex; Nejrotti, Stefano; Echavarren, Antonio M.;
    Departamento: Química Analítica i Química Orgànica
    Autor/es de la URV: ECHAVARREN PABLOS, ANTONIO / Martí Zaragoza, Àlex
    Palabras clave: Urea Terminal alkynes Tandem cyclization Squaramide Silver compounds Silver additives Silver Quinine Phosphorus compounds Phosphines Phosphine ligands Phosphine derivative Phosphine Oxazoles Metabolism Mesoionic carbenes Ligands Ligand Kinetics Hydrohydrazination Hydrogen bond Hydroamination Gold-mediated cyclization Gold compounds Gold Equilibrium acidities Cycloisomerizations Cyclization Complexes Chlorine compounds Chloride complexes Chloride abstraction Catalyst activity Catalysis Associative mechanisms Additives Addition reactions Activation
    Resumen: A library of gold(I) chloride complexes with phosphine ligands incorporating pendant (thio)urea and squaramide H-bond donors was prepared with the aim of promoting chloride abstraction from Au(I) via H-bonding. In the absence of silver additives, complexes bearing squaramides and trifluoromethylated aromatic ureas displayed good catalytic activity in the cyclization of N-propargyl benzamides, as well as in a 1,6-enyne cycloisomerization, a tandem cyclization-indole addition reaction and the hydrohydrazination of phenylacetylene. Kinetic studies and DFT calculations indicate that the energetic span of the reaction is accounted by both the chloride abstraction step, facilitated by the bidentate H-bond donor via an associative mechanism, and the subsequent cyclization step.
    Áreas temáticas: Química Organic chemistry Medicina i Materiais Interdisciplinar General medicine General chemistry Farmacia Engenharias iii Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Ciências agrárias i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Biotecnología Biodiversidade Astronomia / física
    Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
    Direcció de correo del autor: antoniomaria.echavarren@urv.cat alex.marti@estudiants.urv.cat
    Identificador del autor: 0000-0002-6418-7930
    Fecha de alta del registro: 2024-07-27
    Volumen de revista: 27
    Versión del articulo depositado: info:eu-repo/semantics/publishedVersion
    Enlace a la fuente original: https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202101751
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referencia al articulo segun fuente origial: Chemistry-A European Journal. 27 (46): 11989-11996
    Referencia de l'ítem segons les normes APA: Franchino, Allegra; Marti, Alex; Nejrotti, Stefano; Echavarren, Antonio M.; (2021). Silver-Free Au(I) Catalysis Enabled by Bifunctional Urea- and Squaramide-Phosphine Ligands via H-Bonding. Chemistry-A European Journal, 27(46), 11989-11996. DOI: 10.1002/chem.202101751
    DOI del artículo: 10.1002/chem.202101751
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2021
    Tipo de publicación: Journal Publications
  • Palabras clave:

    Catalysis,Chemistry,Chemistry (Miscellaneous),Chemistry, Multidisciplinary,Organic Chemistry
    Urea
    Terminal alkynes
    Tandem cyclization
    Squaramide
    Silver compounds
    Silver additives
    Silver
    Quinine
    Phosphorus compounds
    Phosphines
    Phosphine ligands
    Phosphine derivative
    Phosphine
    Oxazoles
    Metabolism
    Mesoionic carbenes
    Ligands
    Ligand
    Kinetics
    Hydrohydrazination
    Hydrogen bond
    Hydroamination
    Gold-mediated cyclization
    Gold compounds
    Gold
    Equilibrium acidities
    Cycloisomerizations
    Cyclization
    Complexes
    Chlorine compounds
    Chloride complexes
    Chloride abstraction
    Catalyst activity
    Catalysis
    Associative mechanisms
    Additives
    Addition reactions
    Activation
    Química
    Organic chemistry
    Medicina i
    Materiais
    Interdisciplinar
    General medicine
    General chemistry
    Farmacia
    Engenharias iii
    Engenharias ii
    Ciências biológicas iii
    Ciências biológicas ii
    Ciências biológicas i
    Ciências agrárias i
    Chemistry, multidisciplinary
    Chemistry (miscellaneous)
    Chemistry (all)
    Chemistry
    Catalysis
    Biotecnología
    Biodiversidade
    Astronomia / física
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