Metal triflate-promoted allylic substitution reactions of cinnamyl alcohol in the presence of orthoesters and acetals

Dawn R. Chaffey, Carla Alamillo-Ferrer, Thomas E. Davies, Stuart H. Taylor, Nicholas C. O. Tomkinson, Andrew E. 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
Early online date23 Sep 2019
DOIs
Publication statusPublished - 1 Oct 2019

Keywords

  • cinnamyl alcohol
  • orthoesters
  • etherification

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