Articles producció científica> Química Analítica i Química Orgànica

Functional-Group-Tolerant, Silver-Catalyzed N-N Bond Formation by Nitrene Transfer to Amines

  • Dades identificatives

    Identificador: imarina:3654708
    Autors:
    Maestre, LourdesDorel, RuthPablo, OscarEscofet, ImmaSameera, W. M. C.Alvarez, EleuterioMaseras, FeliuMar Diaz-Requejo, M.Echavarren, Antonio M.Perez, Pedro J.
    Resum:
    Silver(I) promotes the highly chemoselective N-amidation of tertiary amines under catalytic conditions to form aminimides by nitrene transfer from PhI¿NTs. Remarkably, this transformation proceeds in a selective manner in the presence of olefins and other functional groups without formation of the commonly observed aziridines or C-H insertion products. The methodology can be applied not only to rather simple tertiary amines but also to complex natural molecules such as brucine or quinine, where the products derived from N-N bond formation were exclusively formed. Theoretical mechanistic studies have shown that this selective N-amidation reaction proceeds through triplet silver nitrenes.
  • Altres:

    Autor segons l'article: Maestre, Lourdes; Dorel, Ruth; Pablo, Oscar; Escofet, Imma; Sameera, W. M. C.; Alvarez, Eleuterio; Maseras, Feliu; Mar Diaz-Requejo, M.; Echavarren, Antonio M.; Perez, Pedro J.;
    Departament: Química Analítica i Química Orgànica
    Autor/s de la URV: ECHAVARREN PABLOS, ANTONIO
    Paraules clau: Silver Bond formation Amines
    Resum: Silver(I) promotes the highly chemoselective N-amidation of tertiary amines under catalytic conditions to form aminimides by nitrene transfer from PhI¿NTs. Remarkably, this transformation proceeds in a selective manner in the presence of olefins and other functional groups without formation of the commonly observed aziridines or C-H insertion products. The methodology can be applied not only to rather simple tertiary amines but also to complex natural molecules such as brucine or quinine, where the products derived from N-N bond formation were exclusively formed. Theoretical mechanistic studies have shown that this selective N-amidation reaction proceeds through triplet silver nitrenes.
    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/
    Adreça de correu electrònic de l'autor: antoniomaria.echavarren@urv.cat
    Identificador de l'autor: 0000-0002-6418-7930
    Data d'alta del registre: 2024-09-07
    Versió de l'article dipositat: info:eu-repo/semantics/publishedVersion
    Enllaç font original: https://pubs.acs.org/doi/abs/10.1021/jacs.6b08219
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referència a l'article segons font original: Journal Of The American Chemical Society. 139 (6): 2216-2223
    Referència de l'ítem segons les normes APA: Maestre, Lourdes; Dorel, Ruth; Pablo, Oscar; Escofet, Imma; Sameera, W. M. C.; Alvarez, Eleuterio; Maseras, Feliu; Mar Diaz-Requejo, M.; Echavarren, A (2017). Functional-Group-Tolerant, Silver-Catalyzed N-N Bond Formation by Nitrene Transfer to Amines. Journal Of The American Chemical Society, 139(6), 2216-2223. DOI: 10.1021/jacs.6b08219
    DOI de l'article: 10.1021/jacs.6b08219
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2017
    Tipus de publicació: Journal Publications
  • Paraules clau:

    Biochemistry,Catalysis,Chemistry,Chemistry (Miscellaneous),Chemistry, Multidisciplinary,Colloid and Surface Chemistry
    Silver
    Bond formation
    Amines
    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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