Belnome, Federico and Garami, Kristóf N. and Varga, Zoltán and Mihály, Judith and Hauk, Pascal and Hergert, Tamás and Keserű, György Miklós and Gallou, Fabrice and Wencel-Delord, Joanna and Ábrányi-Balogh, Péter (2026) Merging Micellar Catalysis and C–H Activation: Silver-Free Direct Arylation of Fluoroarenes in Water. CHEMSUSCHEM, 19 (9). No. e70661. ISSN 1864-5631
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Abstract
The direct arylation of fluoroarenes is a powerful but sustainability-limited transformation, as most established protocols rely on organic solvents and stoichiometric silver additives. Here, we report the first silver-free palladium-catalyzed C–H arylation of fluoroarenes in water containing self-assembled surfactant structures (micelles) as reaction medium. Using the designer surfactant PS-750-M, this sustainable method enables the coupling of diverse pyridines and fluoroarenes under mild conditions, displaying broad functional-group tolerance while fully eliminating organic co-solvents. Mechanistic studies, including kinetics, FT-IR spectroscopy, dynamic light scattering (DLS), and freeze-fracture combined transmission electron microscopy (FF-TEM), reveal the nature of interactions between the catalyst, substrates and distinct micellar domains, providing insight into microenvironmental effects on reactivity and selectivity. The robustness of the catalytic system further allows tandem one-pot sequences, such as C–H arylation/SN Ar reactions, without intermediate workup or adding an additional catalyst. This work demonstrates how merging micellar catalysis with C–H activation unlocks a practical, environmentally responsible platform for cross-coupling chemistry, expanding the utility of aqueous media for sustainable synthesis.
| Item Type: | Article |
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| Additional Information: | Funding Agency and Grant Number: National Research Development and Innovation Fund of the Ministry of Culture and Innovation and the Budapest University of Technology and Economics; Doctoral Excellence Fellowship Programme [DCEP-25-1-BME-53]; Horizon 2020 Framework Programme [860762]; Jnos Bolyai Research Scholarship of the Hungarian Academy of Sciences; Nemzeti Kutatsi Fejlesztsi s Innovcis Hivatal [RRF-2.3.1-21-2022-00015, ADVANCED 150077, TKP2021-EGA-31, 2020-1.1.2-PIACI-KFI-2020-00021, RGH 151414] Funding text: This study was supported by Horizon 2020 Framework Programme (860762) and Nemzeti Kutatasi Fejlesztesi es Innovacios Hivatal (RRF-2.3.1-21-2022-00015, ADVANCED 150077, TKP2021-EGA-31, 2020-1.1.2-PIACI-KFI-2020-00021, RGH 151414). P.A.-B. was supported by the Janos Bolyai Research Scholarship of the Hungarian Academy of Sciences. K.G. was supported by the Doctoral Excellence Fellowship Programme (DCEP-25-1-BME-53) funded by the National Research Development and Innovation Fund of the Ministry of Culture and Innovation and the Budapest University of Technology and Economics. |
| Subjects: | Q Science / természettudomány > QD Chemistry / kémia |
| SWORD Depositor: | MTMT SWORD |
| Depositing User: | MTMT SWORD |
| Date Deposited: | 24 Sep 2026 09:37 |
| Last Modified: | 24 Sep 2026 09:37 |
| URI: | https://real.mtak.hu/id/eprint/247482 |
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