Palladium-Catalyzed Non-Directed C─H Functionalization of Arenes with Trifluoromethylated Olefins

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Stockmann, Levin ; Empel, Claire:
Palladium-Catalyzed Non-Directed C─H Functionalization of Arenes with Trifluoromethylated Olefins.
In: Chemistry : a European Journal. Bd. 31 (2025) Heft 47 . - e01973.
ISSN 1521-3765
DOI der Verlagsversion: https://doi.org/10.1002/chem.202501973

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Abstract

Herein, we report the palladium-catalyzed non-directed C─H functionalization reaction of simple arenes with α-trifluoromethyl styrene derivatives. The application of 2-pyridone ligands increased the yield and selectivity of the alkenylation reaction and enabled a broad scope of different simple arenes and α-trifluoromethyl styrenes (25 examples, up to 94% yield). Overall, a robust reaction is developed as described by a sensitivity screening. Detailed experimental studies on the reaction were performed to further understand the mechanism. Palladium-catalyzed non-directed C─H alkenylation of simple arenes with α-trifluoromethyl styrene derivatives is accomplished using 2-pyridone ligands, which significantly enhances both yield and selectivity. This approach enables efficient functionalization across a wide range of arenes and styrene substrates. Mechanistic studies further clarify the reaction pathway.