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Site-selective cross-coupling of dihalogenated acetophenones and dihalogenated benzophenones with aryl titanium reagents under catalyst control

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Abstract

A method for the selective formation of C2 coupling products via palladium-catalyzed cross-coupling of aryl titanium reagents and dihalogenated benzophenone or dihalogenated acetophenone scaffolds is described. The method uses Pd(dba)2 as catalyst and 2-diisopropylphosphino-2′-dimethylaminobiphenyl as ligand in THF/NMP (3:1) (4.0 cm3) for 10 h at 0 °C. The system can tolerate various functional groups such as aldehydes, esters, etc. In the process of optimizing the coupling method, we also synthesized two new ligands and produced five new monosubstituted aromatic ketones, which appear for the first time in this paper.

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Acknowledgements

The author gratefully acknowledge the financial (YX202215) support from Hebei Chemical & Pharmaceutical College.

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  1. Department of Chemical and Environmental Engineering, Hebei Chemical and Pharmaceutical College, Shijiazhuang, 050026, Hebei, People’s Republic of China

    He Zhang

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Correspondence to He Zhang.

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Zhang, H. Site-selective cross-coupling of dihalogenated acetophenones and dihalogenated benzophenones with aryl titanium reagents under catalyst control. Monatsh Chem 154, 873–885 (2023). https://doi.org/10.1007/s00706-023-03101-3

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