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Redox-Neutral Decarboxylative and Desulfonylative C(sp3) Trifluoromethylation: Method Development and Mechanistic Inquiry

21 April 2023, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Sodium triflinate (CF3SO2Na) is an inexpensive bench stable radical CF3 source that is often activated by external oxidants such as peroxides. However, despite the commercial accessibility of CF3SO2Na, the salt has never been applied to decarboxylative trifluoromethylation due to challenges in controlled cross-radical coupling. We report a redox-neutral approach to decarboxylative C(sp3) trifluoromethylation of carboxylic acid derivatives. Mechanistic inquiry is performed to address the limitations in scope.

Keywords

trifluoromethylation
photoredox catalysis
radical chemistry

Supplementary materials

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Now Published

Redox-Neutral Decarboxylative and Desulfonylative C(sp3) Trifluoromethylation: Method Development and Mechanistic Inquiry [opens in a new tab]
Chris M. Seong, Courtney C. Roberts journal article
The Journal of Organic Chemistry
Online publication date: Jul 19, 2023

Version History

Apr 21, 2023 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2023-8rgnp
D O I: 10.26434/chemrxiv-2023-8rgnp [opens in a new tab]

Funding

National Science Foundation
CHE-1954751

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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