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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202007030
Subject(s) - carbene , ruthenium , alkene , metathesis , reactivity (psychology) , alkyne , chemistry , alkyl , grubbs' catalyst , enyne metathesis , enyne , medicinal chemistry , photochemistry , catalysis , organic chemistry , polymerization , polymer , medicine , alternative medicine , pathology
[(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.