Home / Articles / Generation of aryl radicals by redox processes. Recent progress in the arylation methodology

Generation of aryl radicals by redox processes. Recent progress in the arylation methodology

Dmitry Ivanovich Bugaenko 1
Dmitry Ivanovich Bugaenko
, 
Aleksei Aleksandrovich Volkov 1
Aleksei Aleksandrovich Volkov
, 
Alexander Vakhtangovich Karchava 1
Alexander Vakhtangovich Karchava
, 
Marina Abramovna Yurovskaya 1
Marina Abramovna Yurovskaya
1 Lomonosov Moscow State University, Faculty of Chemistry
10.1070/RCR4959
Published 30 November 2020
Review , RCR4959, Volume 90, Issue 1, 116-170
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Bugaenko D. I. et al. Generation of aryl radicals by redox processes. Recent progress in the arylation methodology // Russian Chemical Reviews. 2020. Vol. 90. No. 1. pp. 116-170.
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Bugaenko D. I., Volkov A. A., Karchava A. V., Yurovskaya M. A. Generation of aryl radicals by redox processes. Recent progress in the arylation methodology // Russian Chemical Reviews. 2020. Vol. 90. No. 1. pp. 116-170.
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TY - JOUR
DO - 10.1070/RCR4959
UR - https://rcr.colab.ws/publications/10.1070/RCR4959
TI - Generation of aryl radicals by redox processes. Recent progress in the arylation methodology
T2 - Russian Chemical Reviews
AU - Bugaenko, Dmitry Ivanovich
AU - Volkov, Aleksei Aleksandrovich
AU - Karchava, Alexander Vakhtangovich
AU - Yurovskaya, Marina Abramovna
PY - 2020
DA - 2020/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 116-170
IS - 1
VL - 90
ER -
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@article{2020_Bugaenko,
author = {Dmitry Ivanovich Bugaenko and Aleksei Aleksandrovich Volkov and Alexander Vakhtangovich Karchava and Marina Abramovna Yurovskaya},
title = {Generation of aryl radicals by redox processes. Recent progress in the arylation methodology},
journal = {Russian Chemical Reviews},
year = {2020},
volume = {90},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4959},
number = {1},
pages = {116--170},
doi = {10.1070/RCR4959}
}
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Bugaenko, Dmitry Ivanovich, et al. “Generation of aryl radicals by redox processes. Recent progress in the arylation methodology.” Russian Chemical Reviews, vol. 90, no. 1, Nov. 2020, pp. 116-170. https://rcr.colab.ws/publications/10.1070/RCR4959.
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Keywords

aromatic acids
aromatic radicals
aryl boronic acids
aryl halides
arylation reactions
arylazosulfones
aryldiazonium salts
arylhydrazines
cathodic reduction
diaryliodonium salts
diazenes
N-arylpyridinium salts
oxidation
photoredox catalysts
reduction
single electron transfer
sulfochlorides
sulfonium salts
triazenes

Abstract

Arylation methods based on the generation and use of aryl radicals have become a rapidly growing field in Arylation methods based on the generation and use of aryl radicals have been a rapidly growing field of research in recent years and currently represent a powerful strategy for carbon--carbon and carbon--heteroatom bond formation. The progress in this field is related to advances in the methods for generation of aryl radicals. The currently used aryl radical precursors include aryl halides, aryldiazonium and diaryliodonium salts, arylcarboxylic acids and their derivatives, arylboronic acids, arylhydrazines, organosulfur(II,VI) compounds and some other compounds. Aryl radicals are generated under mild conditions by single electron reduction or oxidation of precursors induced by conventional reagents, visible light or electric current. A crucial role in the development of the radical arylation methodology belongs to photoredox processes either catalyzed by transition metal complexes or organic dyes or proceeding without catalysts. Unlike the conventional transition metal-catalyzed arylation methods, radical arylation reactions proceed very often at room temperature and have high functional group tolerance. Without claiming to be exhaustive, this review covers the most important advances of the current decade in the generation and synthetic applications of (het)aryl radicals. Examples of reactions are given and mechanistic insights are highlighted.

The bibliography includes 341 references.

Funders

Russian Foundation for Basic Research
19-33-90280

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