Related Experiment Video
Updated: Jan 7, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Electron Donor-Acceptor Complex-Driven Minisci Reactions of N-Heteroaromatic and Inert C(sp3)-H without Brønsted
Meiqiang Li1, Junfeng Yang2, Kaikai Qiao1
1School of Chemistry, Dalian University of Technology, Dalian 116024, PR China.
Abstract:
We report a direct Minisci-type reaction of N-heteroaromatics via electron donor-acceptor (EDA) complex photochemistry. This method employs sulfonium salts as versatile electron acceptors to facilitate Minisci Reactions with unactivated C(sp3)-H bonds (ethers, alkanes, amides) and N-H (amides), P-H (phosphites), and Si-H partners, eliminating the need for prefunctionalized radical precursors, photocatalysts, stoichiometric external oxidants, and Brønsted acids. The aryl radical generated in situ acts as a hydrogen-atom transfer (HAT) agent, abstracting a hydrogen atom from the inert substrate to generate nucleophilic radicals that couple with the N-heteroaromatic. This approach demonstrates broad substrate scope, accommodating diverse N-heteroaromatics (phenanthridines, isoquinolines, quinolines, acridines, benzothiazoles, etc., including acid-sensitive and bioactive molecules such as N-acetyl fasudil) and various inert partners, achieving good to excellent yields.
More Related Videos
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
12:19Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Related Concept Videos
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
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...
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H
Radical Reactivity: Intramolecular vs Intermolecular
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Radical Reactivity: Nucleophilic Radicals