Related Experiment Video
Updated: Jan 17, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Beyond Friedel-Crafts: Spontaneous and Fluoride-Catalyzed Acylation of 2-(Trialkylsilyl)pyridines
Jan Dudziński1, Damian Antoniak1, Kacper Błaziak1,2
1University of Warsaw, Faculty of Chemistry, Pasteura 1, 02-093 Warsaw, Poland.
Abstract:
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.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
14:11Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Related Concept Videos
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene
Limitations of Friedel–Crafts Reactions
Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene
Acid Halides to Carboxylic Acids: Hydrolysis
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
Acid Halides to Esters: Alcoholysis
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.