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

[Display omitted] •Stille acylation using stannanes and acid chlorides gave decarbonylated byproducts.•Only adding triethylsilane suppressed the formation of the byproducts.•Triethylgermanium hydride exhibited better suppressing effect.•The new method provided a versatile method to control Stille ac...

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Veröffentlicht in:Tetrahedron letters 2020-11, Vol.61 (45), p.152466, Article 152466
Hauptverfasser: Higashi, Shoko, Uno, Sota, Ohsuga, Yui, Noumi, Maiko, Saito, Ryota
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Sprache:eng
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Zusammenfassung:[Display omitted] •Stille acylation using stannanes and acid chlorides gave decarbonylated byproducts.•Only adding triethylsilane suppressed the formation of the byproducts.•Triethylgermanium hydride exhibited better suppressing effect.•The new method provided a versatile method to control Stille acylation reactions. 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.152466