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Grubbs Metathesis Enabled by a Light‐Driven gem ‐Hydrogenation of Internal Alkynes
Author(s) -
Biberger Tobias,
Zachmann Raphael J.,
Fürstner Alois
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202007030
Subject(s) - carbene , ruthenium , alkene , metathesis , chemistry , reactivity (psychology) , alkyne , alkyl , grubbs' catalyst , enyne , medicinal chemistry , photochemistry , organic chemistry , catalysis , polymerization , medicine , alternative medicine , pathology , polymer
[(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.