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

Chaffey, Dawn R., Alamillo-Ferrer, Carla, Davies, Thomas E., Taylor, Stuart H., 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 , pp. 15985-15991. 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.

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Chemistry
Cardiff Catalysis Institute (CCI)
Publisher: American Chemical Society
ISSN: 2470-1343
Funders: University of Strathclyde
Date of First Compliant Deposit: 1 October 2019
Date of Acceptance: 22 August 2019
Last Modified: 02 Oct 2019 10:15
URI: http://orca.cf.ac.uk/id/eprint/125813

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