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Synthesis of β2,2-Amino esters via Rh-Catalysed Regioselective Hydroaminomethylation

  • Dades identificatives

    Identificador: imarina:5818675
    Autors:
    Cunillera ARuiz AGodard C
    Resum:
    © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim The synthesis of β2,2-amino esters was successfully achieved via Rh-catalysed regioselective hydroaminomethylation of methyl methacrylate with secondary amines using the neutral precursor [Rh(acac)(CO)2]. In this process, the presence of molecular sieves revealed crucial in order to access the final amino ester. For the synthesis of products containing aniline derivatives, the use of the cationic precursor [Rh(COD)2]BF4 and MeCgPPh phosphine as ligand was necessary in a mixture of toluene/DCE as solvent. Effects of the steric and electronic properties of the amines were observed during this study. Interestingly, poisoning effect of CO in the hydrogenation of the imine intermediate was observed when benzyl amine was used. (Figure presented.).
  • Altres:

    Autor segons l'article: Cunillera A; Ruiz A; Godard C
    Departament: Química Física i Inorgànica
    Autor/s de la URV: Godard, Cyril / Ruiz Manrique, Maria Aurora
    Codi de projecte: CTQ2016-75016-R
    Paraules clau: Β-amino acids Tandem Recent progress Intermolecular amination Hydrogenation Hydroformylation Hydroaminomethylation Derivatives Bonds Beta-amino acids Asymmetric hydrogenation ?-amino acids
    Resum: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim The synthesis of β2,2-amino esters was successfully achieved via Rh-catalysed regioselective hydroaminomethylation of methyl methacrylate with secondary amines using the neutral precursor [Rh(acac)(CO)2]. In this process, the presence of molecular sieves revealed crucial in order to access the final amino ester. For the synthesis of products containing aniline derivatives, the use of the cationic precursor [Rh(COD)2]BF4 and MeCgPPh phosphine as ligand was necessary in a mixture of toluene/DCE as solvent. Effects of the steric and electronic properties of the amines were observed during this study. Interestingly, poisoning effect of CO in the hydrogenation of the imine intermediate was observed when benzyl amine was used. (Figure presented.).
    Àrees temàtiques: Química Organic chemistry Materiais Engenharias iv Engenharias ii Ciências biológicas ii Ciência de alimentos Chemistry, organic Chemistry, applied Catalysis Biodiversidade Astronomia / física
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 16154150
    Adreça de correu electrònic de l'autor: mariaaurora.ruiz@urv.cat cyril.godard@urv.cat
    Identificador de l'autor: 0000-0002-1563-292X 0000-0001-5762-4904
    Data d'alta del registre: 2023-02-18
    Versió de l'article dipositat: info:eu-repo/semantics/publishedVersion
    Enllaç font original: https://onlinelibrary.wiley.com/doi/full/10.1002/adsc.201900642
    Programa de finançament: PROGRAMA ESTATAL DE INVESTIGACIÓN, DESARROLLO E INNOVACIÓN ORIENTADA A LOS RETOS DE LA SOCIEDAD
    Referència a l'article segons font original: Advanced Synthesis & Catalysis. 361 (18): 4201-4207
    Referència de l'ítem segons les normes APA: Cunillera A; Ruiz A; Godard C (2019). Synthesis of β2,2-Amino esters via Rh-Catalysed Regioselective Hydroaminomethylation. Advanced Synthesis & Catalysis, 361(18), 4201-4207. DOI: 10.1002/adsc.201900642
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    Acrònim: ECO2VALCAT
    DOI de l'article: 10.1002/adsc.201900642
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2019
    Acció del programa de finançament: VALORIZACION EFICIENTE DE CO2 A COMBUSTIBLES Y COMPUESTOS DE ALTO VALOR AÑADIDO MEDIANTE CATALISIS HOMOGENEA Y NANO-CATALISIS
    Tipus de publicació: Journal Publications
  • Paraules clau:

    Catalysis,Chemistry, Applied,Chemistry, Organic,Organic Chemistry
    Β-amino acids
    Tandem
    Recent progress
    Intermolecular amination
    Hydrogenation
    Hydroformylation
    Hydroaminomethylation
    Derivatives
    Bonds
    Beta-amino acids
    Asymmetric hydrogenation
    ?-amino acids
    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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