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Palladium-catalyzed cross-coupling of aroyl chlorides with aryl stannanes in the presence of triethylsilane: Efficient access to aromatic ketones

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Abstract Herein, we report the development of a palladium-catalyzed cross-coupling reaction that focuses on the preparation of aromatic ketones. Aroyl chlorides react quickly at 120 °C with aryl stannanes in the… Click to show full abstract

Abstract Herein, we report the development of a palladium-catalyzed cross-coupling reaction that focuses on the preparation of aromatic ketones. Aroyl chlorides react quickly at 120 °C with aryl stannanes in the presence of Pd(PPh3)4 and Et3SiH to efficiently give the corresponding ketones without the formation of significant decarbonylated byproducts. In other words, the decarbonylative side reaction is practically suppressed by simply adding Et3SiH to the reaction mixture, which reduces the amount of biaryl impurities in the products.

Keywords: aryl stannanes; aromatic ketones; aroyl chlorides; palladium catalyzed; catalyzed cross; cross coupling

Journal Title: Tetrahedron Letters
Year Published: 2020

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