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

MPS-Authors
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Biberger,  Tobias
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Zachmann,  Raphael J.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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anie202007030-sup-0001-misc_information.pdf
(Supplementary material), 11MB

Citation

Biberger, T., Zachmann, R. J., & Fürstner, A. (2020). Grubbs Metathesis Enabled by a Light‐Driven gem‐Hydrogenation of Internal Alkynes. Angewandte Chemie International Edition, 59(42), 18423-18429. doi:10.1002/anie.202007030.


Cite as: http://hdl.handle.net/21.11116/0000-0007-650E-9
Abstract
[(NHC)(cymene)RuCl2] (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 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.