Articles producció científica> Química Física i Inorgànica

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

  • Identification data

    Identifier: imarina:5818675
    Authors:
    Cunillera ARuiz AGodard C
    Abstract:
    © 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.).
  • Others:

    Author, as appears in the article.: Cunillera A; Ruiz A; Godard C
    Department: Química Física i Inorgànica
    URV's Author/s: Godard, Cyril / Ruiz Manrique, Maria Aurora
    Project code: CTQ2016-75016-R
    Keywords: Β-amino acids Tandem Recent progress Intermolecular amination Hydrogenation Hydroformylation Hydroaminomethylation Derivatives Bonds Beta-amino acids Asymmetric hydrogenation ?-amino acids
    Abstract: © 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.).
    Thematic Areas: Química Organic chemistry Materiais Engenharias iv Engenharias ii Ciências biológicas ii Ciência de alimentos Chemistry, organic Chemistry, applied Catalysis Biodiversidade Astronomia / física
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 16154150
    Author's mail: mariaaurora.ruiz@urv.cat cyril.godard@urv.cat
    Author identifier: 0000-0002-1563-292X 0000-0001-5762-4904
    Record's date: 2023-02-18
    Papper version: info:eu-repo/semantics/publishedVersion
    Link to the original source: https://onlinelibrary.wiley.com/doi/full/10.1002/adsc.201900642
    Funding program: PROGRAMA ESTATAL DE INVESTIGACIÓN, DESARROLLO E INNOVACIÓN ORIENTADA A LOS RETOS DE LA SOCIEDAD
    Papper original source: Advanced Synthesis & Catalysis. 361 (18): 4201-4207
    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
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Acronym: ECO2VALCAT
    Article's DOI: 10.1002/adsc.201900642
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2019
    Funding program action: VALORIZACION EFICIENTE DE CO2 A COMBUSTIBLES Y COMPUESTOS DE ALTO VALOR AÑADIDO MEDIANTE CATALISIS HOMOGENEA Y NANO-CATALISIS
    Publication Type: Journal Publications
  • Keywords:

    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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