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Direct electrochemical hydrodefluorination of trifluoromethylketones enabled by non-protic conditions

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Abstract

CF2H groups are unique due to the combination of their lipophilic and hydrogen bonding properties. The strength of H-bonding is determined by the group to which it is appended. Several functional groups have been explored in this context including O, S, SO and SO2 to tune the intermolecular interaction. Difluoromethyl ketones are under-studied in this context, without a broadly accessible method for their preparation. Herein, we describe the development of an electrochemical hydrodefluorination of readily accessible trifluoromethylketones. The single-step reaction at deeply reductive potentials is uniquely amenable to challenging electron-rich substrates and reductively sensitive functionality. Key to this success is the use of non-protic conditions enabled by an ammonium salt that serves as a reductively stable, masked proton source. Analysis of their H-bonding has revealed difluoromethyl ketones to be potentially highly useful dual H-bond donor/acceptor moieties.

Graphical abstract: Direct electrochemical hydrodefluorination of trifluoromethylketones enabled by non-protic conditions

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Supplementary files

Article information


Submitted
18 Mar 2021
Accepted
22 Jun 2021
First published
06 Jul 2021

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2021, Advance Article
Article type
Edge Article

Direct electrochemical hydrodefluorination of trifluoromethylketones enabled by non-protic conditions

J. R. Box, A. P. Atkins and A. J. J. Lennox, Chem. Sci., 2021, Advance Article , DOI: 10.1039/D1SC01574E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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