Related Experiment Video
Updated: Dec 31, 2025

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Nickel-Catalyzed, para-Selective, Radical-Based Alkylation of Aromatic Ketones
Jie Wang1, Yu-Bo Pang1, Na Tao1
1Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology , Soochow University , Suzhou 215123 , China.
Abstract:
A direct, para-selective, radical-based alkylation of aromatic ketones with alkanes has been developed using a nickel catalyst with oxamide as the ligand. Acetophenones bearing electron-withdrawing substituents were functionalized directly with simple alkanes with high para-selectivity while acetophenones with electron-donating groups were mainly para-functionalized. A mechanistic study indicated that C-H bond activation of the aromatic ring may be the rate-determining step of the reaction.
Related Concept Videos
α-Alkylation of Ketones via Enolate Ions
Radical Anti-Markovnikov Addition to Alkenes: Overview
Radical Reactivity: Nucleophilic Radicals
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...
Radical Reactivity: Electrophilic Radicals
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...

