Evidencing an inner-sphere mechanism for NHC-Au(I)- catalyzed carbene-transfer reactions from ethyl diazoacetate
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Abstract
Kinetic experiments based on the measurement of nitrogen evolution in the reaction of ethyl diazoacetate (N2CHCO2Et, 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 CHCO2Et 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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Bibliographic citation
Romero Fructos-Vázquez, M., Urbano Baena, J., Díaz Requejo, M.M., Pérez Romero, P.J.: "Evidencing an inner-sphere mechanism for NHC-Au(I)- catalyzed carbene-transfer reactions from ethyl diazoacetate". Beilstein Journal of Organic Chemistry. Vol. 11, págs. 2254–2260, (2015). DOI: 10.3762/bjoc.11.245
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