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. 2019 Dec 6;21(23):9759-9762.
doi: 10.1021/acs.orglett.9b03950. Epub 2019 Nov 14.

Direct Hydrofluorination of Methallyl Alkenes Using a Methanesulfonic Acid/Triethylamine Trihydrofluoride Combination

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Direct Hydrofluorination of Methallyl Alkenes Using a Methanesulfonic Acid/Triethylamine Trihydrofluoride Combination

Xavier Bertrand et al. Org Lett. .

Abstract

The use of a methanesulfonic acid/triethylamine trihydrofluoride combination for the direct hydrofluorination of methallyl-containing substrates is reported. Under those metal-free conditions that use readily available, cheap, and easy to handle reagents, a range of methallyl alkenes could be converted to their corresponding tertiary fluoride in up to 78% yield. Finally, a promising result for the adaptation of this chemistry to continuous flow conditions is reported.

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