Metal triflate-promoted allylic substitution reactions of cinnamyl alcohol in the presence of orthoesters and acetals
Chaffey, Dawn R. and Alamillo-Ferrer, Carla and Davies, Thomas E. and Taylor, Stuart H. and Tomkinson, Nicholas C. O. and Graham, Andrew E. (2019) Metal triflate-promoted allylic substitution reactions of cinnamyl alcohol in the presence of orthoesters and acetals. ACS Omega, 4 (14). pp. 15985-15991. ISSN 2470-1343 (https://doi.org/10.1021/acsomega.9b02059)
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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.
ORCID iDs
Chaffey, Dawn R., Alamillo-Ferrer, Carla ORCID: https://orcid.org/0000-0003-3607-846X, Davies, Thomas E., Taylor, Stuart H., Tomkinson, Nicholas C. O. ORCID: https://orcid.org/0000-0002-5509-0133 and Graham, Andrew E.;-
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Item type: Article ID code: 70363 Dates: DateEvent1 October 2019Published23 September 2019Published Online22 August 2019AcceptedSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry Depositing user: Pure Administrator Date deposited: 31 Oct 2019 10:03 Last modified: 13 Oct 2024 00:38 Related URLs: URI: https://strathprints.strath.ac.uk/id/eprint/70363