Evidencing an inner-sphere mechanism for NHC-Au(I)-catalyzed carbene-transfer reactions from ethyl diazoacetate

Kinetic experiments based on the measurement of nitrogen evolution in the reaction of ethyl diazoacetate (N(2)CHCO(2)Et, EDA) and styrene or methanol catalyzed by the [IPrAu](+) core (IPr = 1,3-bis(diisopropylphenyl)imidazole-2-ylidene) have provided evidence that the transfer of the carbene group C...

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Detalles Bibliográficos
Autores principales: Fructos, Manuel R, Urbano, Juan, Díaz-Requejo, M Mar, Pérez, Pedro J
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4660976/
https://www.ncbi.nlm.nih.gov/pubmed/26664649
http://dx.doi.org/10.3762/bjoc.11.245
Descripción
Sumario:Kinetic experiments based on the measurement of nitrogen evolution in the reaction of ethyl diazoacetate (N(2)CHCO(2)Et, EDA) and styrene or methanol catalyzed by the [IPrAu](+) core (IPr = 1,3-bis(diisopropylphenyl)imidazole-2-ylidene) have provided evidence that the transfer of the carbene group CHCO(2)Et to the substrate (styrene or methanol) takes place in the coordination sphere of Au(I) by means of an inner-sphere mechanism, in contrast to the generally accepted proposal of outer-sphere mechanisms for Au(I)-catalyzed reactions.

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