Electrochemical Vicinal Difluorination of Alkenes: Sustainable, Scalable, and Amenable to Electron-rich Substrates

16 October 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Fluorinated alkyl groups are important motifs in bioactive compounds, positively influencing pharmacokinetics, potency and F conformation. The oxidative difluorination of alkenes represents an H 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 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 (in the presence of nucleophilic fluoride and HFIP) using an ‘ex-cell’ approach, which avoids the oxidative decomposition of the substrate. The more sustainable conditions give good to excellent yields of product in up to decagram scales


Hypervalent iodine
green chemistry

Supplementary materials

Supporting information Difluorination Lennox


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