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

Biberger Tobias | Zendy; Zachmann Raphael J. | Zendy; Fürstner Alois | Zendy

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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.

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