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  • The Mechanism of Markovnikov-Selective Epoxide Hydrogenolysis Catalysed by Ruthenium PNN and PNP Pincer Complexes

    • The Mechanism of Markovnikov-Selective Epoxide Hydrogenolysis Catalysed by Ruthenium PNN and PNP Pincer Complexes

    Title The Mechanism of Markovnikov-Selective Epoxide Hydrogenolysis Catalysed by Ruthenium PNN and PNP Pincer Complexes
    Authors Marianna C. Head, Benjamin T. Joseph, Jason M. Keith, Anthony R. Chianese
    Magazine Organometallics
    Date 02/27/2023
    DOI 10.1021/acs.organomet.2c00503
    Introduction Recent interest in homogeneous catalysis of epoxide hydrogenolysis producing alcohols has led to the development of catalysts for selective Markovnikov or anti-Markovnikov alcohol formation. Markovnikov-selective catalysts typically involve Noyori/Shvo-type bifunctional catalysis with RuH/NH or FeH/OH structures. Proposed mechanisms suggest cooperative C–O bond hydrogenolysis with a metal hydride and acidic ligand pendant group, akin to polar double-bond hydrogenation. Through combined computational and experimental studies, we explore epoxide hydrogenolysis mechanisms catalysed by Noyori-type PNP and PNN ruthenium complexes. Our findings indicate the previously proposed bifunctional pathway for these ruthenium systems is energetically unfavourable. Instead, ring-opening occurs via nucleophilic attack of ruthenium hydride on the epoxide carbon, without ligand N–H group involvement. Rate law and energy barriers predicted by DFT align with kinetic study results.
    Quote Marianna C. Head, Benjamin T. Joseph and Jason M. Keith et al. The Mechanism of Markovnikov-Selective Epoxide Hydrogenolysis Catalysed by Ruthenium PNN and PNP Pincer Complexes. Organometallics. 2023. Vol. 42(5):347-356. DOI: 10.1021/acs.organomet.2c00503
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