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6.1.39.5.3 Variation 3: Arylations and Alkylations of Acid Halides

DOI: 10.1055/sos-SD-006-00976

Kaufmann, D. E.; Köster, M.Science of Synthesis, (200561225.

Ketones are available from the reaction of tetraalkyl- or trialkyl(aryl)borates with acyl halides. This reaction is very useful for obtaining ketones that are otherwise difficult to synthesize, e.g. via the FriedelCrafts route. To suppress alkyl transfer, the use of sec-alkylboranes, such as tricyclopentylborane, is helpful. Lithium is essential as the counterion because borates, obtained from Grignard reagents and trialkylboranes, usually give O-alkylated arylketones in low yields only (Scheme 13).[‌17‌,‌53‌] Copper(I) as the counterion enhances the tendency of intermolecular transfer of organic groups.

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