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

Lourdes Maestre, Ruth Dorel, Óscar Pablo, Imma Escofet, W. M.C. Sameera, Eleuterio Álvarez, Feliu Maseras, M. Mar Díaz-Requejo, Antonio M. Echavarren, Pedro J. Pérez

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Abstract

© 2017 American Chemical Society. 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.
Original languageEnglish
Pages (from-to)2216-2223
JournalJournal of the American Chemical Society
Volume139
Issue number6
DOIs
Publication statusPublished - 15 Feb 2017

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    Maestre, L., Dorel, R., Pablo, Ó., Escofet, I., Sameera, W. M. C., Álvarez, E., Maseras, F., Díaz-Requejo, M. M., Echavarren, A. M., & Pérez, P. J. (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. https://doi.org/10.1021/jacs.6b08219