Articles producció científica> Química Física i Inorgànica

Intermolecular Allene Functionalization by Silver-Nitrene Catalysis

  • Dades identificatives

    Identificador: imarina:7979618
    Autors:
    Rodriguez, Manuel R.Besora, MariaMolina, FranciscoMaseras, FeliuMar Diaz-Requejo, M.Perez, Pedro J.
    Resum:
    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.
  • Altres:

    Autor segons l'article: Rodriguez, Manuel R.; Besora, Maria; Molina, Francisco; Maseras, Feliu; Mar Diaz-Requejo, M.; Perez, Pedro J.;
    Departament: Química Física i Inorgànica
    Autor/s de la URV: Besora Bonet, Maria
    Paraules clau: Singlet Regio Chemistry Carbethoxynitrene C-h Bonds Aziridination Amination
    Resum: 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.
    Àrees temàtiques: 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
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 00027863
    Adreça de correu electrònic de l'autor: maria.besora@urv.cat
    Identificador de l'autor: 0000-0002-6656-5827
    Data d'alta del registre: 2023-02-19
    Versió de l'article dipositat: info:eu-repo/semantics/acceptedVersion
    Enllaç font original: https://pubs.acs.org/doi/10.1021/jacs.0c04395
    Referència a l'article segons font original: Journal Of The American Chemical Society. 142 (30): 13062-13071
    Referència de l'ítem segons les normes 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
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    DOI de l'article: 10.1021/jacs.0c04395
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2020
    Tipus de publicació: Journal Publications
  • Paraules clau:

    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
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