Articles producció científica> Química Analítica i Química Orgànica

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

  • Identification data

    Identifier: PC:2587
    Authors:
    Antonio M. EchavarrenLourdes MaestreRuth DorelÓscar PabloImma EscofetW. M. C. SameeraEleuterio ÁlvarezFeliu MaserasM. Mar Díaz-RequejoPedro J. Perez
    Abstract:
    DOI: 10.1021/jacs.6b08219 URL: http://pubs.acs.org/doi/abs/10.1021/jacs.6b08219 Filiació URV: SI Memòria
  • Others:

    Author, as appears in the article.: Antonio M. Echavarren; Lourdes Maestre; Ruth Dorel; Óscar Pablo; Imma Escofet; W. M. C. Sameera; Eleuterio Álvarez; Feliu Maseras; M. Mar Díaz-Requejo; Pedro J. Perez
    Department: Química Analítica i Química Orgànica
    URV's Author/s: ECHAVARREN PABLOS, ANTONIO MARIA; Lourdes Maestre; Ruth Dorel; Óscar Pablo; Imma Escofet; W. M. C. Sameera; Eleuterio Álvarez; Feliu Maseras; M. Mar Díaz-Requejo; Pedro J. Perez
    Keywords: Amines Bond formation Silver
    Abstract: 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.
    Thematic Areas: Química Química Chemistry
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 0002-7863
    Author identifier: n/a; n/a; n/a; n/a; n/a; 0000-0003-0213-0688; n/a; 0000-0001-8806-2019; n/a; n/a
    Record's date: 2017-03-01
    Last page: 2223
    Journal volume: 139
    Papper version: info:eu-repo/semantics/publishedVersion
    Link to the original source: http://pubs.acs.org/doi/abs/10.1021/jacs.6b08219
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Article's DOI: 10.1021/jacs.6b08219
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2017
    First page: 2216
    Publication Type: Article Artículo Article
  • Keywords:

    Amines
    Plata
    Amines
    Bond formation
    Silver
    Química
    Química
    Chemistry
    0002-7863
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