Photoelectrochemical Iron(III) Catalysis for Late‐Stage C─H Fluoroalkylations

Chemo- and site-selective functionalization of complex molecules poses a fundamental challenge. Herein, we introduce a resource-economic photoelectrocatalysis strategy to enable versatile direct fluoroalkylations catalyzed by Earth-abundant iron and paired with the hydrogen evolution reaction (HER). Notably, the devised approach proved amenable to versatile late-stage C─H fluoroalkylations of bio-relevant heterocycles, such as xanthines, nucleobases, and nucleosides. Mechanistic studies supported a ligand-to-metal charge transfer-induced formation of the fluoroalkyl radical.

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Publication Details

Journal
Angewandte Chemie International Edition
Published
2025-04-14
DOI
https://doi.org/10.1002/anie.202504143
Citations
14
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
11.07

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article

Photoelectrochemical Iron(III) Catalysis for Late‐Stage C─H Fluoroalkylations

Vladimir Motornov, Tristan von Münchow, Claudia Stückl, Lutz Ackermann et al.
14 citations
Angewandte Chemie International Edition
Fluorine in Organic Chemistry
11.07
article

Photoelectrochemical Iron(III) Catalysis for Late‐Stage C─H Fluoroalkylations

Vladimir Motornov, Tristan von Münchow, Claudia Stückl, Lutz Ackermann, Sven Trienes, Simonetta Resta, João C. A. Oliveira, Zhipeng Lin, Zhi Liu
article en
14 citations

Abstract

Chemo- and site-selective functionalization of complex molecules poses a fundamental challenge. Herein, we introduce a resource-economic photoelectrocatalysis strategy to enable versatile direct fluoroalkylations catalyzed by Earth-abundant iron and paired with the hydrogen evolution reaction (HER). Notably, the devised approach proved amenable to versatile late-stage C─H fluoroalkylations of bio-relevant heterocycles, such as xanthines, nucleobases, and nucleosides. Mechanistic studies supported a ligand-to-metal charge transfer-induced formation of the fluoroalkyl radical.

Angewandte Chemie International EditionVol. 64(25)
German Centre for Cardiovascular Research (DE), University of Göttingen (DE)
Alexander von Humboldt-Stiftung, Deutsches Zentrum für Herz-Kreislaufforschung, Università degli Studi di Milano, Deutsche Forschungsgemeinschaft, Georg-August-Universität Göttingen, Gottfried Wilhelm Leibniz Universität Hannover, Leibniz-Gemeinschaft, Erasmus+
Openalex Percentile: Top 1%
Fluorine in Organic Chemistry
11.07
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