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  • Hydrogenative Cycloisomerisation and Sigmatropic Rearrangement Reactions of Cationic Ruthenium Carbenes Formed by Catalytic Alkyne gem‐Hydrogenation

    • Hydrogenative Cycloisomerisation and Sigmatropic Rearrangement Reactions of Cationic Ruthenium Carbenes Formed by Catalytic Alkyne gem‐Hydrogenation

    Title Hydrogenative Cycloisomerisation and Sigmatropic Rearrangement Reactions of Cationic Ruthenium Carbenes Formed by Catalytic Alkyne gem‐Hydrogenation
    Authors Dr. Tobias Biberger, Stephan N. Hess, Dr. Markus Leutzsch, Prof. Alois Fürstner
    Magazine Angewandte Chemie (International Ed. in English)
    Date 01/03/2022
    DOI 10.1002/anie.202113827
    Introduction The research explores the gem‐hydrogenation of propargyl alcohol derivatives using [Cp XRu(MeCN) 3]PF 6 catalysts, resulting in the formation of cationic pianostool ruthenium carbene complexes. These complexes are notably electrophilic, capable of attacking tethered olefins to produce cyclopentene products. Unlike traditional transformations, cyclopropanation or metathesis do not interfere with this process. If the carbenes possess suitable propargylic substituents, they undergo ([2,3]‐sigmatropic) rearrangements, yielding enol esters or alkenyl halides. These pathways represent novel advancements in hydrogenation chemistry. The proposed mechanisms are supported by labelling experiments and spectroscopic data, particularly PHIP NMR spectroscopy, confirming the reactions are initiated by unconventional gem‐hydrogenation events.
    Quote Tobias Biberger, Stephan N. Hess and Markus Leutzsch et al. Hydrogenative Cycloisomerisation and Sigmatropic Rearrangement Reactions of Cationic Ruthenium Carbenes Formed by Catalytic Alkyne gem‐Hydrogenation. Angew. Chem. Int. Ed. Engl. 2022. DOI: 10.1002/anie.202113827
    Element Ruthenium (Ru)
    Industry Chemical & Pharmacy
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