Related Experiment Video
Updated: Jan 13, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Electricity-Induced Radical 7-endo-Cyclization from Aryldiazonium Salts: Synthesis of Trifluoromethylated Azepines
Wei Wei1, Wenjing Ma2, Qi Li2
1Guangxi Key Laboratory of Bioactive Molecules Research and Evaluation and Guangxi Key Laboratory of Pharmaceutical Precision Detection and Screening, School of Pharmacy, Guangxi Medical University, 22 Shuangyong Road, Nanning 530021, China.
Abstract:
Nitrogen-containing heterocycles represent pivotal structural motifs that pervade diverse pharmaceuticals and bioactive agents. Arenediazonium salts function as versatile building blocks for the synthesis of such heterocycles while preserving the N2 moiety. Herein, we report an electrochemical strategy that facilitates the efficient assembly of structurally complex, multi-heteroatom heterocyclic systems, enabling the simultaneous formation of C═N bonds and construction of seven-membered rings, from trifluoromethanesulfinates and aryl diazonium salts. The design of this reaction was guided by the principles underlying radical polarity matching and a sustainable synthesis. This mild, electrochemically triggered radical process provides an atom-economical pathway to a diverse range of fluorinated seven-membered N-heterocycles, obviating the need for stoichiometric oxidants.
More Related Videos
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
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...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

