102004-64-8Relevant articles and documents
Functional-Group-Tolerant, Silver-Catalyzed N-N Bond Formation by Nitrene Transfer to Amines
Maestre, Lourdes,Dorel, Ruth,Pablo, óscar,Escofet, Imma,Sameera,álvarez, Eleuterio,Maseras, Feliu,Díaz-Requejo, M. Mar,Echavarren, Antonio M.,Pérez, Pedro J.
supporting information, p. 2216 - 2223 (2017/02/23)
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.