Related Experiment Video
Updated: Sep 13, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
HFIP-Assisted Denitrogenative Radical Fragmentation Pathway of Areneazo-2-(2-nitro)propanes: Cross-Coupling of Aryl
Daeun Kim1, Hun Young Kim2, Kyungsoo Oh1
1Center for Metareceptome Research, Graduate School of Pharmaceutical Sciences, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul 06974, Republic of Korea.
Abstract:
The HFIP-assisted denitrogenative radical fragmentation of areneazo-2-(2-nitro)propanes, a safer alternative to diazonium salts, generated dinitrogen, nitrogen monoxide, acetone, and aryl radicals. These in situ generated aryl radicals participated in [4 + 2] benzannulations to form phenanthrenes and in diverse cross-coupling reactions, including Sandmeyer-type C-Br/C-Bpin/C-S/C-Se/C-P and C-C bond formations. TEMPO-trapping experiments confirmed their transient nature, enabling versatile approaches to radical-mediated C-C and C-X bond construction under mild and practical conditions.
Related Concept Videos
Radical Reactivity: Overview
Radical Reactivity: Nucleophilic Radicals
Radical Anti-Markovnikov Addition to Alkenes: Mechanism
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Mass Spectrometry: Alkyne Fragmentation
Radical Formation: Overview
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the...

