RT Journal Article
T1 Reaction of Alkynes and Azides: Not Triazoles Through Copper–Acetylides but Oxazoles Through Copper–Nitrene Intermediates
A1 Haldón Hermoso, Estela
A1 Besora, María
A1 Cano Rico, Israel
A1 Cambeiro, Xacobe C.
A1 Pericàs, Miquel A.
A1 Maseras, Feliu
A1 Nicasio Jaramillo, María Carmen
A1 Pérez Romero, Pedro José
AB Well-defined copper(I) complexes of composition [Tpm*,BrCu(NCMe)]BF4 (Tpm*,Br=tris(3,5-dimethyl-4-bromo-pyrazolyl)methane) or [Tpa*Cu]PF6 (Tpa*=tris(3,5-dimethyl-pyrazolylmethyl)amine) catalyze the formation of 2,5-disubstituted oxazoles from carbonyl azides and terminal alkynes in a direct manner. This process represents a novel procedure for the synthesis of this valuable heterocycle from readily available starting materials, leading exclusively to the 2,5-isomer, attesting to a completely regioselective transformation. Experimental evidence and computational studies have allowed the proposal of a reaction mechanism based on the initial formation of a copper–acyl nitrene species, in contrast to the well-known mechanism for the copper-catalyzed alkyne and azide cycloaddition reactions (CuAAC) that is triggered by the formation of a copper–acetylide complex.
PB Wiley
SN 0947-6539
SN 1521-3765 (electrónico)
YR 2014
FD 2014
LK https://hdl.handle.net/10272/22781
UL https://hdl.handle.net/10272/22781
LA eng
NO Haldón, E., Besora, M., Cano, I., Cambeiro, X. C., Pericàs, M. A., Maseras, F., Nicasio, M. C., & Pérez, P. J. (2014). Reaction of Alkynes and Azides: Not Triazoles Through Copper–Acetylides but Oxazoles Through Copper–Nitrene Intermediates. In Chemistry – A European Journal (Vol. 20, Issue 12, pp. 3463–3474). Wiley. https://doi.org/10.1002/chem.201303737
NO We thank MINECO (CTQ2011–28942-CO2–01, CTQ2011–27033, CTQ2008–00947/BQU and CTQ2012–38594-C02–01) and Consolider Ingenio (2010 CSD2006–0003), Fondos Feder, DEC (2009SGR259, 2009SGR623), Junta de Andalucía (Proyectos P07-FQM-02745 and P10-FQM-06292), and the ICIQ Foundation.
DS Repositorio Institucional de la Universidad de Huelva
RD 1 jun 2026