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Electrochemical Vicinal Difluorination of Alkenes: Scalable and Amenable to Electron-Rich Substrates

Research output: Contribution to journalArticle

Original languageEnglish
Pages (from-to)1155-1160
Number of pages6
JournalAngewandte Chemie - International Edition
Volume59
Issue number3
Early online date28 Nov 2019
DOIs
DateAccepted/In press - 6 Nov 2019
DateE-pub ahead of print - 28 Nov 2019
DatePublished (current) - 13 Jan 2020

Abstract

Fluorinated alkyl groups are important motifs in bioactive compounds, positively influencing pharmacokinetics, potency and conformation. The oxidative difluorination of alkenes represents an important strategy for their preparation, yet current methods are limited in their alkene-types and tolerance of electron-rich, readily oxidized functionalities, as well as in their safety and scalability. Herein, we report a method for the difluorination of a number of unactivated alkene-types that is tolerant of electron-rich functionality, giving products that are otherwise unattainable. Key to success is the electrochemical generation of a hypervalent iodine mediator using an “ex-cell” approach, which avoids oxidative substrate decomposition. The more sustainable conditions give good to excellent yields in up to decagram scales.

    Research areas

  • hypervalent iodine, oxidation, electrochemistry, fluorination, green chemistry

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    Rights statement: This is the final published version of the article (version of record). It first appeared online via Wiley at https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201912119 . Please refer to any applicable terms of use of the publisher.

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