Metal Triflate-Promoted Allylic Substitution Reactions of Cinnamyl Alcohol in the Presence of Orthoesters and Acetals

Dawn Chaffey, Carla Alamillo-Ferrer, Thomas E. Davies, Stuart H. Taylor, Nicholas C. O. Tomkinson, Andrew Graham

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    Abstract

    The product distribution of ethers formed from the reaction of cinnamyl alcohol with orthoesters in the presence of indium (III) triflate (InOTf)3 is dependent on both the reaction temperature and catalyst loading. Carrying out the reaction at room temperature under low loadings of the catalyst leads to a facile reaction generating the unexpected secondary allyl ether as the major product. In contrast, carrying out the reaction under higher catalyst loadings at elevated temperatures provides the expected primary linear ether in high yield and with excellent selectivity. The etherification reaction is also effective in the presence of acetals and ketals in place of orthoesters and allows for the development of the procedure to encompass a telescoped etherification protocol in which the acetal is generated in situ.
    Original languageEnglish
    Pages (from-to)15985-15991
    Number of pages7
    JournalACS Omega
    Volume4
    Issue number14
    DOIs
    Publication statusPublished - 23 Sep 2019

    Keywords

    • Etherification

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