INVESTIGADORES
MOGLIE Yanina Fernanda
congresos y reuniones científicas
Título:
Alkenes as Azido Precursors for the One-Pot Synthesis of 1,2,3-Triazoles Catalyzed by Copper Nanoparticles on Activated Carbon
Autor/es:
YANINA MOGLIE; FRANCISCO ALONSO; GABRIEL RADIVOY; MIGUEL YUS
Lugar:
Alicante
Reunión:
Congreso; VI International School on Organometallic Chemistry Marcial Moreno Mañas; 2013
Institución organizadora:
Universidad de Alicante, Equipo de Consolider Ingenio 2010-Orfeo Team CSD2007-00006
Resumen:
Recently,
we introduced a catalyst consisting of oxidized copper nanoparticles on
activated carbon (CuNPs/C), readily prepared under mild conditions, which
exhibited a high versatility in the multicomponent click synthesis of
1,2,3-triazoles in water. Not only organic halides but diazonium salts,
anilines, and epoxides were successfully used as azide precursors in the CuAAC.
We want to present herein the first one-pot transformation of inactivated
olefins into 1,2,3-triazoles by taking advantage of two consecutive click
reactions: (a) the ring opening of in-situ generated episulfonium ions by the
azide anion and (b) the reaction of the in-situ generated azides with alkynes
catalyzed by CuNPs/C.
High
yields of the b-methylsulfanyl triazoles have been attained using
CuNPs/C as catalyst, with other commercial copper catalysts being completely
inactive. The versatility of the methylsulfanyl group has been demonstrated
through a series of synthetic transformations, including the direct access to
1-vinyl and 4-monosubstituted triazoles.