Related Experiment Video
Updated: Nov 2, 2025

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Cobalt-catalyzed aminocarbonylation of (hetero)aryl halides promoted by visible light
Alexander M Veatch1, Erik J Alexanian1
1Department of Chemistry, The University of North Carolina at Chapel Hill Chapel Hill North Carolina 27599 USA eja@email.unc.edu.
Abstract:
The catalytic aminocarbonylation of (hetero)aryl halides is widely applied in the synthesis of amides but relies heavily on the use of precious metal catalysis. Herein, we report an aminocarbonylation of (hetero)aryl halides using a simple cobalt catalyst under visible light irradiation. The reaction extends to the use of (hetero)aryl chlorides and is successful with a broad range of amine nucleophiles. Mechanistic investigations are consistent with a reaction proceeding via intermolecular charge transfer involving a donor-acceptor complex of the substrate and cobaltate catalyst.
Related Concept Videos
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution
Nucleophilic Aromatic Substitution: Elimination–Addition
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...
α-Halogenation of Carboxylic Acid Derivatives: Overview
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
