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钯催化芳烃与三氟甲基化烯烃的非定向C─H官能团化反应

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

作者信息

Stockmann Levin, Empel Claire

机构信息

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.

University of Bayreuth, Universitätsstraße 30, 95447, Bayreuth, Germany.

出版信息

Chemistry. 2025 Aug 21;31(47):e01973. doi: 10.1002/chem.202501973. Epub 2025 Jul 23.

DOI:10.1002/chem.202501973
PMID:40702805
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12376254/
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.

摘要

在此,我们报道了简单芳烃与α-三氟甲基苯乙烯衍生物的钯催化非导向C─H官能化反应。2-吡啶酮配体的应用提高了烯基化反应的产率和选择性,并适用于多种不同的简单芳烃和α-三氟甲基苯乙烯(25个实例,产率高达94%)。总体而言,如敏感性筛选所述,开发了一种稳健的反应。对该反应进行了详细的实验研究以进一步了解其机理。使用2-吡啶酮配体实现了简单芳烃与α-三氟甲基苯乙烯衍生物的钯催化非导向C─H烯基化反应,这显著提高了产率和选择性。该方法能够在广泛的芳烃和苯乙烯底物上进行高效官能化。机理研究进一步阐明了反应途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1db/12376254/c3262dd7b5b7/CHEM-31-e01973-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1db/12376254/026068572881/CHEM-31-e01973-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1db/12376254/5a7910560799/CHEM-31-e01973-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1db/12376254/48cfd21500de/CHEM-31-e01973-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1db/12376254/c3262dd7b5b7/CHEM-31-e01973-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1db/12376254/026068572881/CHEM-31-e01973-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1db/12376254/5a7910560799/CHEM-31-e01973-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1db/12376254/48cfd21500de/CHEM-31-e01973-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a1db/12376254/c3262dd7b5b7/CHEM-31-e01973-g005.jpg

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