Related Experiment Video
Updated: Feb 15, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Regioselective Reaction of Heterocyclic N-Oxides, an Acyl Chloride, and Cyclic Thioethers
Przemyslaw Frei1, D Heulyn Jones1, Steven T Kay1
1WestCHEM, Department of Pure and Applied Chemistry, Thomas Graham Building, University of Strathclyde , 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.
Abstract:
Treatment of electron deficient pyridine N-oxides with 4-nitrobenzoyl chloride and a cyclic thioether in the presence of triethylamine leads to the corresponding 2-functionalized product in up to a 74% isolated yield. The transformation can also be accomplished with alternative nitrogen containing heterocycles, including quinolines, pyrimidines, and pyrazines. To expand the scope of the transformation, diisopropyl ether can be used as the reaction medium to allow for the use of solid thioether substrates.
Related Concept Videos
Oxidation-Reduction Reactions
Oxidation Numbers
Phase I Oxidative Reactions: Overview
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Reactions at the Benzylic Position: Oxidation and Reduction
Basicity of Heterocyclic Aromatic Amines

