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

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide 2-(Trialkylsilyl)pyridines react spontaneously with acyl chlorides to give 2-pyridyl ketones in high yields. The process consists of four elementary steps of N -acylation, desilylation, C -acylation, and N -deacylation and results in a selective monosubstitution at the carbonyl group. The key step in this mechanism is the intrinsic generation of a stabilized ylide (Hammick intermediate), which acts as a nucleophile. For the functionalization of complex molecules, an alternative fluoride-catalyzed protocol utilizing more stable acyl fluorides has been developed.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c03140

Authors: Jan Dudziński, Damian Antoniak, Kacper Błaziak, Michał Barbasiewicz

Institution: University of Warsaw

Language: English

Topic: Chemical Synthesis and Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Narodowe Centrum Nauki, Uniwersytet Warszawski, Infrastruktura PL-Grid