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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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
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author Fructos, Manuel R
Urbano, Juan
Díaz-Requejo, M Mar
Pérez, Pedro J
author_facet Fructos, Manuel R
Urbano, Juan
Díaz-Requejo, M Mar
Pérez, Pedro J
author_sort Fructos, Manuel R
collection PubMed
description 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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spelling pubmed-46609762015-12-09 Evidencing an inner-sphere mechanism for NHC-Au(I)-catalyzed carbene-transfer reactions from ethyl diazoacetate Fructos, Manuel R Urbano, Juan Díaz-Requejo, M Mar Pérez, Pedro J Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2015-11-20 /pmc/articles/PMC4660976/ /pubmed/26664649 http://dx.doi.org/10.3762/bjoc.11.245 Text en Copyright © 2015, Fructos et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Fructos, Manuel R
Urbano, Juan
Díaz-Requejo, M Mar
Pérez, Pedro J
Evidencing an inner-sphere mechanism for NHC-Au(I)-catalyzed carbene-transfer reactions from ethyl diazoacetate
title Evidencing an inner-sphere mechanism for NHC-Au(I)-catalyzed carbene-transfer reactions from ethyl diazoacetate
title_full Evidencing an inner-sphere mechanism for NHC-Au(I)-catalyzed carbene-transfer reactions from ethyl diazoacetate
title_fullStr Evidencing an inner-sphere mechanism for NHC-Au(I)-catalyzed carbene-transfer reactions from ethyl diazoacetate
title_full_unstemmed Evidencing an inner-sphere mechanism for NHC-Au(I)-catalyzed carbene-transfer reactions from ethyl diazoacetate
title_short Evidencing an inner-sphere mechanism for NHC-Au(I)-catalyzed carbene-transfer reactions from ethyl diazoacetate
title_sort evidencing an inner-sphere mechanism for nhc-au(i)-catalyzed carbene-transfer reactions from ethyl diazoacetate
topic Full Research Paper
url 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
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