Related Experiment Video
Updated: Nov 30, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Metal-Free Three-Component Coupling Reaction of Ketones with Electron-rich Arenes and Selenium Dioxide for the
Kmendashisha Wanniang1, O Risuklang Shangpliang1, Ibakyntiew D Marpna1
1Centre for Advanced Studies in Chemistry, Department of Chemistry, North-Eastern Hill University, Shillong 793022, India.
Abstract:
A metal-free three-component coupling reaction of aryl alkyl/alkyl ketones, SeO2, and phenols/anisoles is described. This multicomponent reaction provides a straightforward and facile pathway for the synthesis of α-((4-hydroxy/methoxyphenyl)selanyl)-aryl alkyl/alkyl ketones in the presence of p-toluenesulfonic acid for the C-Se bond formation process. The method offers an attractive and simple procedure using commonly available shelf reagents to deliver organoselenides that, to our knowledge, are being reported here for the first time.
Related Concept Videos
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
α-Alkylation of Ketones via Enolate Ions
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

