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Flow electrochemistry: a safe tool for fluorine chemistry

Winterson, Bethan, Rennigholtz, Tim and Wirth, Thomas ORCID: https://orcid.org/0000-0002-8990-0667 2021. Flow electrochemistry: a safe tool for fluorine chemistry. Chemical Science 12 (26) , pp. 9053-9059. 10.1039/D1SC02123K

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Abstract

The heightened activity of compounds containing fluorine, especially in the field of pharmaceuticals, provides major impetus for the development of new fluorination procedures. A scalable, versatile, and safe electrochemical fluorination protocol is conferred. The strategy proceeds through a transient (difluoroiodo)arene, generated by anodic oxidation of an iodoarene mediator. Even the isolation of iodine(III) difluorides was facile since electrolysis was performed in the absence of other reagents. A broad range of hypervalent iodine mediated reactions were achieved in high yields by coupling the electrolysis step with downstream reactions in flow, surpassing limitations of batch chemistry. (Difluoroiodo)arenes are toxic and suffer from chemical instability, so the uninterrupted generation and immediate use in flow is highly advantageous. High flow rates facilitated productivities of up to 834 mg h−1 with vastly reduced reaction times. Integration into a fully automated machine and in-line quenching was key in reducing the hazards surrounding the use of hydrofluoric acid.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Royal Society of Chemistry
ISSN: 2041-6520
Funders: EPSRC
Date of First Compliant Deposit: 16 June 2021
Date of Acceptance: 4 June 2021
Last Modified: 09 Nov 2022 11:08
URI: https://orca.cardiff.ac.uk/id/eprint/141933

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