Articles producció científica> Química Física i Inorgànica

Intermolecular Allene Functionalization by Silver-Nitrene Catalysis

  • Identification data

    Identifier: imarina:7979618
    Authors:
    Rodriguez, Manuel R.Besora, MariaMolina, FranciscoMaseras, FeliuMar Diaz-Requejo, M.Perez, Pedro J.
    Abstract:
    Under silver catalysis conditions, using [Tp*Ag-,Ag-Br](2) as the catalyst precursor, allenes react with PhI=NTs in the first example of efficient metal-mediated intermolecular nitrene transfer to such substrates. The nature of the substituent at the allene seems crucial for the reaction outcome since arylallenes are converted into azetidine derivatives, whereas methylene aziridines are the products resulting from alkylallenes. Mechanistic studies allow proposing that azetidines are formed through unstable cyclopropylimine intermediates, which further incorporate a second nitrene group, both processes being silver-mediated. Methylene aziridines from alkylallenes derive from catalytic nitrene addition to the allene double bonds. Both routes have resulted to be productive for further synthetic transformations affording aminocyclopropanes.
  • Others:

    Author, as appears in the article.: Rodriguez, Manuel R.; Besora, Maria; Molina, Francisco; Maseras, Feliu; Mar Diaz-Requejo, M.; Perez, Pedro J.;
    Department: Química Física i Inorgànica
    URV's Author/s: Besora Bonet, Maria
    Keywords: Singlet Regio Chemistry Carbethoxynitrene C-h Bonds Aziridination Amination
    Abstract: Under silver catalysis conditions, using [Tp*Ag-,Ag-Br](2) as the catalyst precursor, allenes react with PhI=NTs in the first example of efficient metal-mediated intermolecular nitrene transfer to such substrates. The nature of the substituent at the allene seems crucial for the reaction outcome since arylallenes are converted into azetidine derivatives, whereas methylene aziridines are the products resulting from alkylallenes. Mechanistic studies allow proposing that azetidines are formed through unstable cyclopropylimine intermediates, which further incorporate a second nitrene group, both processes being silver-mediated. Methylene aziridines from alkylallenes derive from catalytic nitrene addition to the allene double bonds. Both routes have resulted to be productive for further synthetic transformations affording aminocyclopropanes.
    Thematic Areas: Química Materiais Interdisciplinar General chemistry Farmacia Engenharias iv Engenharias iii Engenharias ii Colloid and surface chemistry Ciências biológicas ii Ciências biológicas i Ciências agrárias i Ciência de alimentos Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Biochemistry Astronomia / física
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 00027863
    Author's mail: maria.besora@urv.cat
    Author identifier: 0000-0002-6656-5827
    Record's date: 2023-02-19
    Papper version: info:eu-repo/semantics/acceptedVersion
    Link to the original source: https://pubs.acs.org/doi/10.1021/jacs.0c04395
    Papper original source: Journal Of The American Chemical Society. 142 (30): 13062-13071
    APA: Rodriguez, Manuel R.; Besora, Maria; Molina, Francisco; Maseras, Feliu; Mar Diaz-Requejo, M.; Perez, Pedro J.; (2020). Intermolecular Allene Functionalization by Silver-Nitrene Catalysis. Journal Of The American Chemical Society, 142(30), 13062-13071. DOI: 10.1021/jacs.0c04395
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Article's DOI: 10.1021/jacs.0c04395
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2020
    Publication Type: Journal Publications
  • Keywords:

    Biochemistry,Catalysis,Chemistry,Chemistry (Miscellaneous),Chemistry, Multidisciplinary,Colloid and Surface Chemistry
    Singlet
    Regio
    Chemistry
    Carbethoxynitrene
    C-h
    Bonds
    Aziridination
    Amination
    Química
    Materiais
    Interdisciplinar
    General chemistry
    Farmacia
    Engenharias iv
    Engenharias iii
    Engenharias ii
    Colloid and surface chemistry
    Ciências biológicas ii
    Ciências biológicas i
    Ciências agrárias i
    Ciência de alimentos
    Chemistry, multidisciplinary
    Chemistry (miscellaneous)
    Chemistry (all)
    Chemistry
    Catalysis
    Biochemistry
    Astronomia / física
  • Documents:

  • Cerca a google

    Search to google scholar