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September 21, 2025Organic LettersOpen Access

Beyond Friedel–Crafts: Spontaneous and Fluoride-Catalyzed Acylation of 2-(Trialkylsilyl)pyridines

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Spontaneous acylation yields 2-pyridyl ketones in high yields, utilizing an intrinsic Hammick intermediate.
The process involves four steps: N-acylation, desilylation, C-acylation, and N-deacylation for selective monosubstitution.
An alternative fluoride-catalyzed method with acyl fluorides has been developed for functionalizing complex molecules.
This reaction mechanism highlights the significance of stabilized ylides as nucleophiles for effective acylation.

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Spontaneous acylation generates 2-pyridyl ketones, while fluoride-catalyzed methods improve stability.

Dudzinski et al. (2025) studied this question.

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