Related Experiment Video
Updated: Jan 28, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
One-pot, modular approach to functionalized ketones via nucleophilic addition/Buchwald-Hartwig amination strategy
Jorn de Jong1, Dorus Heijnen1, Hugo Helbert1
1Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands. b.l.feringa@rug.nl.
Abstract:
A general one-pot procedure for the 1,2-addition of organolithium reagents to amides followed by the Buchwald-Hartwig amination with in situ released lithium amides is presented. In this work amides are used as masked ketones, revealed by the addition of organolithium reagents which generates a lithium amide, suitable for subsequent Buchwald-Hartwig coupling in the presence of a palladium catalyst. This methodology allows for rapid, efficient and atom economic synthesis of aminoarylketones in good yields.
Related Concept Videos
Nucleophilic Addition to the Carbonyl Group: General Mechanism
A stronger nucleophile can directly attack the electrophilic center, the carbonyl carbon. The HOMO orbital of the nucleophile interacts with the LUMO (π* antibonding) orbital present on the carbonyl carbon. This interaction breaks the π bond and shifts the π...
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
Preparation of Amines: Reductive Amination of Aldehydes and Ketones
Nucleophilic Aromatic Substitution: Elimination–Addition
Functional Groups
Aldehydes and Ketones with Amines: Enamine Formation Mechanism

