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Grubbs Metathesis Enabled by a Light‐Driven gem‐Hydrogenation of Internal Alkynes

[(NHC)(cymene)RuCl(2)] (NHC=N‐heterocyclic carbene) complexes instigate a light‐driven gem‐hydrogenation of internal alkynes with concomitant formation of discrete Grubbs‐type ruthenium carbene species. This unorthodox reactivity mode is harnessed in the form of a “hydrogenative metathesis” reaction...

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Detalles Bibliográficos
Autores principales: Biberger, Tobias, Zachmann, Raphael J., Fürstner, Alois
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7589215/
https://www.ncbi.nlm.nih.gov/pubmed/32608043
http://dx.doi.org/10.1002/anie.202007030
Descripción
Sumario:[(NHC)(cymene)RuCl(2)] (NHC=N‐heterocyclic carbene) complexes instigate a light‐driven gem‐hydrogenation of internal alkynes with concomitant formation of discrete Grubbs‐type ruthenium carbene species. This unorthodox reactivity mode is harnessed in the form of a “hydrogenative metathesis” reaction, which converts an enyne substrate into a cyclic alkene. The intervention of ruthenium carbenes formed in the actual gem‐hydrogenation step was proven by the isolation and crystallographic characterization of a rather unusual representative of this series carrying an unconfined alkyl group on a disubstituted carbene center.