Related Experiment Video
Updated: Jan 10, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Gomberg-Bachmann C-H Arylation of Cyclic Nitrones Enabled by an Organic Base
Alexey A Akulov1, Andrey A Pershin1, Anastasia A Deleva1
1Institute of Chemical Engineering, Ural Federal University, 19 Mira Str., Ekaterinburg 620062, Russia.
None:
We report the first direct C(sp2)-H functionalization of cyclic aldonitrones (namely 2H-/4H-imidazole N-oxides) using aryl diazonium tetrafluoroborates, with the process being solely promoted by N,N-diisopropylethylamine (DIPEA). This Gomberg-Bachmann-type protocol allowed 37 arylated nitrones to be obtained in 33-86% yields. A mechanistic study involving LCMS and EPR techniques has confirmed the radical essence of the approach, whereas the XRD analysis of some reaction products has revealed the unconventional π-hole tetrel bonding characteristic of their supramolecular arrangement.
More Related Videos
07:06A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
Related Concept Videos
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Nucleophilic Aromatic Substitution: Elimination–Addition
Electrophilic Aromatic Substitution: Nitration of Benzene
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...
Base-Promoted α-Halogenation of Aldehydes and Ketones