English   español  
Por favor, use este identificador para citar o enlazar a este item: http://hdl.handle.net/10261/133820
COMPARTIR / IMPACTO:
Estadísticas
logo share SHARE logo core CORE   Add this article to your Mendeley library MendeleyBASE

Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Exportar a otros formatos:
Título

Rhodium(I)-N-heterocyclic carbene catalyst for selective coupling of N-vinylpyrazoles with alkynes via C-H activation

AutorAzpíroz, Ramón; Rubio-Pérez, Laura ; Giuseppe, Andrea di ; Passarelli, Vincenzo ; Lahoz, Fernando J. ; Castarlenas, Ricardo ; Pérez-Torrente, Jesús J. ; Oro, Luis A.
Palabras claveC−H activation
C−C coupling
N-heterocyclic carbene
Pyrazole
Rhodium
Fecha de publicación2014
EditorAmerican Chemical Society
CitaciónACS Catalysis 4(12): 4244-4253 (2014)
ResumenThe complex [Rh(μ-Cl)(IPr)(η2-coe)]2 {IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-carbene, coe = cis-cyclooctene} efficiently catalyzes the coupling of alkynes and N-vinylpyrazole via C–H activation, leading to Markovnikov-selective butadienylpyrazole derivatives under mild conditions. A straightforward approach to cross-conjugated acyclic trienes is also operative through a one-pot alkyne dimerization-hydrovinylation tandem reaction. The proposed mechanism involves C–H activation of vinylpyrazole directed by nitrogen coordination to the metallic center. Subsequent alkyne coordination, insertion, and reductive elimination steps lead to the coupling products. Several key intermediates participating in the catalytic cycle have been detected and characterized, including a κ-N, η2-C═C coordinated vinylpyrazole complex and a RhIII-hydride-alkenyl species resulting from the C–H activation of the vinylpyrazole.
Versión del editorhttp://dx.doi.org/10.1021/cs501366q
URIhttp://hdl.handle.net/10261/133820
DOI10.1021/cs501366q
Identificadoresdoi: 10.1021/cs501366q
e-issn: 2155-5435
Aparece en las colecciones: (ISQCH) Artículos
Ficheros en este ítem:
Fichero Descripción Tamaño Formato  
N-Vinylpyrazoles.pdf2,17 MBAdobe PDFVista previa
Visualizar/Abrir
Mostrar el registro completo
 

Artículos relacionados:


NOTA: Los ítems de Digital.CSIC están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.