Related Experiment Video
Updated: Jan 7, 2026
![[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)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Visible-Light-Induced Amination of Pyridylphosphonium Salts: Synthesis of Heteroarylamines via Radical-Radical
Yulong Ran1, Lei Li2, Yunbo Jia1
1School of Petrochemical Engineering, Liaoning Petrochemical University, Fushun 113001, P. R. China.
Abstract:
The development of operationally simple and efficient synthetic methodologies for constructing heteroarylamines is highly valuable in modern synthetic chemistry. Herein, we describe a visible-light-induced, mild, oxidant- and reductant-free radical-radical coupling between pyridylphosphonium salts and arylamines for their synthesis. This protocol exhibits excellent regioselectivity, broad substrate scope, and good functional group tolerance, enabling the late-stage functionalization of complex drug molecules and providing a sustainable pathway to valuable aromatic amines. Mechanistic studies indicate that DABCO acts as a key mediator, facilitating two sequential single-electron transfer (SET) and deprotonation processes.
Related Concept Videos
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Preparation of Amines: Alkylation of Ammonia and Amines
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
Acid Halides to Amides: Aminolysis
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...

