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

Sayad Doobary, Alexi T. Sedikides, Henry P. Caldora, Darren L. Poole, Alastair J. J. Lennox*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

9 Citations (Scopus)
127 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)1155-1160
Number of pages6
JournalAngewandte Chemie - International Edition
Volume59
Issue number3
Early online date28 Nov 2019
DOIs
Publication statusPublished - 13 Jan 2020

Structured keywords

  • BCS and TECS CDTs

Keywords

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

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