Controlling the selectivity and efficiency of the hydrogen borrowing reaction by switching between rhodium and iridium catalysts

Danfeng Wang, Roy T. McBurney, Indrek Pernik, Barbara A. Messerle

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    16 Citations (Scopus)
    6 Downloads (Pure)

    Abstract

    The catalytic alkylation of ketones with alcohols via the hydrogen borrowing methodology (HB) has the potential to be a highly efficient approach for forming new carbon-carbon bonds. However, this transformation can result in more than one product being formed. The work reported here utilises bidentate triazole-carbene ligated iridium and rhodium complexes as catalysts for the selective formation of alkylated ketone or alcohol products. Switching from an iridium centre to a rhodium centre in the complex resulted in significant changes in product selectivity. Other factors - base, base loading, solvent and reaction temperature - were also investigated to tune the selectivity further. The optimised conditions were used to demonstrate the scope of the reaction across 17 ketones and 14 alcohols containing a variety of functional groups. A series of mechanistic investigations were performed to probe the reasons behind the product selectivity, including kinetic and deuterium studies.

    Original languageEnglish
    Pages (from-to)13989-13999
    Number of pages11
    JournalJournal of the Chemical Society. Dalton Transactions
    Volume48
    Issue number37
    DOIs
    Publication statusPublished - 7 Oct 2019

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