Articles producció científicaQuímica Analítica i Química Orgànica

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

  • Identification data

    Identifier:  PC:2587
    Handle: https://hdl.handle.net/20.500.11797/PC2587
    Authors:  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
    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.

  • Others:

    Link to the original source: http://pubs.acs.org/doi/abs/10.1021/jacs.6b08219
    Article's DOI: 10.1021/jacs.6b08219
    Journal publication year: 2017
    Entity: Universitat Rovira i Virgili
    Paper version: info:eu-repo/semantics/publishedVersion
    Record's date: 2017-03-01
    First page: 2216
    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
    Department: Química Analítica i Química Orgànica
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Publication Type: Article
    Last page: 2223
    ISSN: 0002-7863
    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
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Journal volume: 139
    Thematic Areas: Chemistry