RT Journal Article
T1 Functional-Group-Tolerant, Silver-Catalyzed N–N Bond Formation by Nitrene Transfer to Amines
A1 Maestre Cera, Lourdes
A1 Dorel, Ruth
A1 Pablo, Óscar
A1 Escofet, Imma
A1 Sameera, W. M. C.
A1 Álvarez, Eleuterio
A1 Maseras, Feliu
A1 Díaz Requejo, María Mar
A1 Echavarren, Antonio M.
A1 Pérez Romero, Pedro José
AB Silver(I) promotes the highly chemoselective N-amidation of tertiary amines under catalytic conditionsto form aminimides by nitrene transfer from PhI=NTs. Remarkably, this transformation proceeds in aselective manner in the presence of olefins and other functional groups without formation of the commonlyobserved aziridines or C-H insertion products. The methodology can be applied not only to rather simple tertiaryamines but also to complex natural molecules such as brucine or quinine, where the products derived fromN-N formation were exclusively formed. Theoretical mechanistic studies have shown that this selective Namidationreaction proceeds through triplet silver-nitrenes.
PB American Chemical Society
SN 0002-7863
SN 1520-5126
YR 2017
FD 2017
LK http://hdl.handle.net/10272/16191
UL http://hdl.handle.net/10272/16191
LA eng
NO Maestre, L., Dorel, R., Pablo, Ó., Escofet, I., Sameera, W. M. C., Álvarez, E., … 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
NO We thank MINECO for Grants CTQ2014-52769-C3-1-R, CTQ2013-42106-P, CTQ2014-57761-R, Severo Ochoa Excellence Accreditation 2014-2018 (SEV-2013-0319), Red Intecat (CTQ2014-52974-REDC), FPI fellowship (L.M.), the European Research Council (Advanced Grant No. 321066), the AGAUR (2014 SGR 818), and CERCA Program/Generalitat de Catalunya. We also thank Dr. Tania Jimenez for additional experiments and the ICIQ X-ray diffraction unit for the crystal structures of compounds 5-7, 17b, 21, and 25.
DS Repositorio Institucional de la Universidad de Huelva
RD 1 jun 2026