Related Experiment Video
Updated: Jan 8, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Aromatization-Driven C-C Bond Cleavage of Unstrained Ketone Access to Vinyl Sulfones
Hong-Chen Wang1, Hong Fu1, Peng-Fei Zhao1
1State Key Laboratory of Natural Product Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
Abstract:
Ketones, as simple and readily available bulk chemicals, have long been the focus of synthetic chemistry. Herein, we report a new protocol for the radical deconstruction of unstrained ketones by in situ conversion of them into dihydroquinoline (DHQ) prearomatics and subsequent oxidative aromatization. By combination with subsequent radical cascade reactions of DABSO and aryl acetylene, this protocol can convert acyclic and cyclic ketones and even ketone-containing complex natural products into a series of valuable vinyl sulfones in a one-pot, two-step method.
More Related Videos
Related Concept Videos
Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt...
C–C Bond Cleavage: Retro-Aldol Reaction
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.
Alkynes to Carboxylic Acids: Oxidative Cleavage
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
Structures of Aldehydes and Ketones
In aldehydes (Figures 1a and 1b), the...
Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes

