Home / Articles / Direct nucleophilic functionalization of $\mathrm{C(sp^2)-H}$ bonds in (hetero)arenes by electrochemical methods

Direct nucleophilic functionalization of $\mathrm{C(sp^2)-H}$ bonds in (hetero)arenes by electrochemical methods

Alexandr Vladimirovich Shchepochkin 1
Alexandr Vladimirovich Shchepochkin
, 
Oleg Nikolaevich Chupakhin 1, 2
Oleg Nikolaevich Chupakhin
,  , 
Vladimir Anushavanovich Petrosyan 3
Vladimir Anushavanovich Petrosyan
1 I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Sciences, Ekaterinburg
2 Ural Federal University named after the First President of Russia B. N. Yeltsin, Ekaterinburg
3 N.D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences
10.1070/RC2013v082n08ABEH004386
Published 30 November 2012
Communication , Volume 82, Issue 8, 747-771
37
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Shchepochkin A. V. et al. Direct nucleophilic functionalization of $\mathrm{C(sp^2)-H}$ bonds in (hetero)arenes by electrochemical methods // Russian Chemical Reviews. 2013. Vol. 82. No. 8. pp. 747-771.
GOST all authors (up to 50)
Copy cite
Shchepochkin A. V., Chupakhin O. N., Charushin V. N., Petrosyan V. A. Direct nucleophilic functionalization of $\mathrm{C(sp^2)-H}$ bonds in (hetero)arenes by electrochemical methods // Russian Chemical Reviews. 2013. Vol. 82. No. 8. pp. 747-771.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.1070/RC2013v082n08ABEH004386
UR - https://rcr.colab.ws/publications/10.1070/RC2013v082n08ABEH004386
TI - Direct nucleophilic functionalization of $\mathrm{C(sp^2)-H}$ bonds in (hetero)arenes by electrochemical methods
T2 - Russian Chemical Reviews
AU - Shchepochkin, Alexandr Vladimirovich
AU - Chupakhin, Oleg Nikolaevich
AU - Charushin, Valery Nikolaevich
AU - Petrosyan, Vladimir Anushavanovich
PY - 2013
DA - 2012/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 747-771
IS - 8
VL - 82
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
Copy cite
@article{2013_Shchepochkin,
author = {Alexandr Vladimirovich Shchepochkin and Oleg Nikolaevich Chupakhin and Valery Nikolaevich Charushin and Vladimir Anushavanovich Petrosyan},
title = {Direct nucleophilic functionalization of $\mathrm{C(sp^2)-H}$ bonds in (hetero)arenes by electrochemical methods},
journal = {Russian Chemical Reviews},
year = {2013},
volume = {82},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC2013v082n08ABEH004386},
number = {8},
pages = {747--771},
doi = {10.1070/RC2013v082n08ABEH004386}
}
MLA
Cite this
MLA
Copy cite
Shchepochkin, Alexandr Vladimirovich, et al. “Direct nucleophilic functionalization of $\mathrm{C(sp^2)-H}$ bonds in (hetero)arenes by electrochemical methods.” Russian Chemical Reviews, vol. 82, no. 8, Nov. 2013, pp. 747-771. https://rcr.colab.ws/publications/10.1070/RC2013v082n08ABEH004386.
Views / Visits / Downloads
25 / 25 / 4

Abstract

Published data on electrochemical methods and approaches used for direct functionalization of the $\mathrm{C(sp^{2})-H}$ bond through nucleophilic displacement of hydrogen ($\mathrm{S_{N}^{H}}$-reactions) are surveyed and described systematically. The most important features of preparative electrochemical processes are considered. The attention is concentrated on the synthetic potential of the discussed transformations.

Bibliography 133 references.

References

1.
Palladium(II)-Catalyzed CH Activation/CC Cross-Coupling Reactions: Versatility and Practicality
Chen X., Engle K., Wang D., Yu J.
Angewandte Chemie - International Edition , 2009
2.
2
A. A. Krasnovskii
Zhur. Fiz. Khim. , 1956
3.
3
M. F. Shostakovskii
"Prostye Vinilovye Efiry" (Vinyl Ethers) , 1952
4.
4
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
5.
Nucleophilic substitution of hydrogen in azines
Chupakhin O.N., Charushin V.N., van der Plas H.C.
Tetrahedron , 1988
6.
Nucleophilic aromatic substitution of hydrogen and related reactions
Charushin V.N., Chupakhin O.N.
Mendeleev Communications , 2007
7.
SNH methodology and new approaches to condensed heterocyclic systems
Charushin V.N., Chupakhin O.N.
Pure and Applied Chemistry , 2004
8.
8
V. N. Kondrat'ev
"Kinetika Reaktsii v Gazovoi Faze" (Kinetics of Reactions in the Gas Phase) , 1959
9.
9
V. H. Lynch
Carnegie Inst. Year Book , 1954
10.
Vicarious nucleophilic substitution of hydrogen
Makosza M., Winiarski J.
Accounts of Chemical Research , 1987
11.
Progress in the studies of oxidation of dihydropyridines and their analogues
Matern A.I., Charushin V.N., Chupakhin O.N.
Russian Chemical Reviews , 2007
12.
Petrosyan Vladimir Anushavanovich
Mendeleev Communications , 2011
13.
10.1021/cr020086+
14.
From synthetic organic chemistry to electrochemistry
Lund H.
Journal of Solid State Electrochemistry , 2010
15.
Organic electrosynthesis: a promising green methodology in organic chemistry
Frontana-Uribe B.A., Little R.D., Ibanez J.G., Palma A., Vasquez-Medrano R.
Green Chemistry , 2010
16.
16
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
17.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
18.
Pursuing practical elegance in chemical synthesis
Noyori R.
Chemical Communications , 2005
20.
20
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
21.
21
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
22.
22
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
23.
23
N. V. Vostrilova
Dokl. Akad. Nauk Uzbek. SSR , 1958
27.
27
A. A. Krasnovskii
Biofizika , 1956
28.
10.1002/1521-3765(20010417)7:8<1712::AID-CHEM17120>3.0.CO;2-G
29.
The crystal structure of the σ-complex of 4,6-dinitrobenzofuroxan and potassium 2-nitropropenide
Terrier F., Lelièvre J., Chatrousse A.P., Boubaker T., Bachet B., Cousson A.
Journal of the Chemical Society Perkin Transactions 2 , 1992
31.
Electrochemical Synthesis of Nitroaromatic Ketones
Gallardo I., Guirado G., Marquet J.
European Journal of Organic Chemistry , 2002
33.
Cation-radicals in the electrochemical oxidation of 1,2,6-trimethyl-3,5-diacetyl-1,2-dihydropyridines
Stradyn' Y., Gavars R., Baumane L., Duburs G.
Chemistry of Heterocyclic Compounds , 1997
34.
Special Features of the Electrochemical Oxidation of Substituted 4-Carboxy-1,4-dihydropyridines
Stradins J., Baumane L., Kalnins A., Uldrikis J., Bisenieks E., Poikans J., Duburs G.
Chemistry of Heterocyclic Compounds , 2000
36.
Electrochemical oxidation of 4-monoalkyl-substituted 1,4-dihydropyridines
Turovska B., Goba I., Turovskis I., Grinberga S., Belyakov S., Stupnikova S., Liepinsh E., Stradins J.
Chemistry of Heterocyclic Compounds , 2008
37.
Solid state photochemistry of 1,4-dihydropyridines
Memarian H.R., Mirjafari A.
Bioorganic and Medicinal Chemistry Letters , 2005
39.
Electrochemical synthesis of 1,2,3,4,4,5,6-substituted 1,4-dihydropyridines
Goba I., Turovska B., Stradins J., Turovskis I., Liepinsh E., Belyakov S.
Chemistry of Heterocyclic Compounds , 2007
44.
Electrochemical synthesis of alkyl nitroaromatic compounds.
Gallardo I., Guirado G., Marquet J.
Journal of Organic Chemistry , 2002
45.
Alkylation of nitroaromatics with tetraalkylborate ion via electrochemical oxidation.
Gallardo I., Guirado G., Marquet J.
Journal of Organic Chemistry , 2003
46.
MII/MIII-Catalyzed ortho-Fluoroalkylation of 2-Phenylpyridine
Dudkina Y.B., Mikhaylov D.Y., Gryaznova T.V., Sinyashin O.G., Vicic D.A., Budnikova Y.H.
European Journal of Organic Chemistry , 2012
47.
Key green chemistry research areas—a perspective from pharmaceutical manufacturers
Constable D.J., Dunn P.J., Hayler J.D., Humphrey G.R., Leazer, Jr. J.L., Linderman R.J., Lorenz K., Manley J., Pearlman B.A., Wells A., Zaks A., Zhang T.Y.
Green Chemistry , 2007
48.
Anodic Oxidation of Mono- and Disubstituted 1,4-Dimethoxybenzenes
Zeng C., Becker J.Y.
Journal of Organic Chemistry , 2004
49.
Mechanism of nucleophilic substitution of hydrogen in azines IV. Role of one-electron transfer in reactions with arylamines
Chupakhin O.N., Charushin V.N., Sosonkin I.M., Kovalev E.G., Kalb G.L., Postovskii I.Y.
Chemistry of Heterocyclic Compounds , 1977
53.
53
D. Porretand E. Rabinowitch
Nature , 1937
54.
Palladium-Catalyzed Cross-Coupling Reactions in Total Synthesis
Nicolaou K.C., Bulger P.G., Sarlah D.
Angewandte Chemie - International Edition , 2005
55.
Synthesis of Light-Emitting Conjugated Polymers for Applications in Electroluminescent Devices
Grimsdale A.C., Leok Chan K., Martin R.E., Jokisz P.G., Holmes A.B.
Chemical Reviews , 2009
58.
Modern Strategies in Electroorganic Synthesis
Yoshida J., Kataoka K., Horcajada R., Nagaki A.
Chemical Reviews , 2008
60.
Efficient anodic and direct phenol-arene C,C cross-coupling: the benign role of water or methanol.
Kirste A., Elsler B., Schnakenburg G., Waldvogel S.R.
Journal of the American Chemical Society , 2012
61.
Electrochemical Conversions of 2-Methyl-3-nitro-4-phenylquinoline, Its Quinolinium Salts, and Hydrogenated Derivatives
Stradins J., Baumane L., Vigante B., Duburs G.
Chemistry of Heterocyclic Compounds , 2001
63.
Synthesis and Electrochemical Oxidation of Nitriles of 4-Aryl-2-carbamoylmethylthio-5-ethoxycarbonyl-1,4-dihydropyridine-3-carboxylic Acids
Baumane L., Krauze A., Chernova L., Sile L., Duburs G., Stradins J.
Chemistry of Heterocyclic Compounds , 2003
64.
Synthesis, Cardiovascular Activity, and Electrochemical Oxidation of Nitriles of 5-Ethoxycarbonyl-2-methylthio-1,4-dihydropyridine-3-carboxylic Acid
Krauze A., Baumane L., Sile L., Chernova L., Vilums M., Vitolina R., Duburs G., Stradins J.
Chemistry of Heterocyclic Compounds , 2004
65.
Synthesis, Structure, and Electrochemical Characteristics of 4-Aryl-2-carbamoylmethylthio-5-ethoxycarbonyl-1,4-dihydropyridine-3-carboxylic Acid Nitriles
Baumane L., Krauze A., Belyakov S., Sile L., Chernova L., Griga M., Duburs G., Stradins J.
Chemistry of Heterocyclic Compounds , 2005
66.
Electrochemical oxidation of hydrogenated indolizines and their precursors in chemical synthesis—quaternized pyridyldihydropyridines
Turovska B., Stradiņš J., Strazdiņš I., Makarova N., Plotniece A., Duburs G.
Electrochimica Acta , 1997
67.
Electrochemical Oxidation of Compounds Containing 1,4-Dihydropyridine and Pyridinium Rings — Analogs of Gene Transfection Agents
Turovska B., Stradins J., Turovskis I., Plotniece A., Shmidlers A., Duburs G.
Chemistry of Heterocyclic Compounds , 2004
68.
Oxidation of cationic 1,4-dihydropyridine derivatives as model compounds for putative gene delivery agents
Plotniece A., Pajuste K., Kaldre D., Cekavicus B., Vigante B., Turovska B., Belyakov S., Sobolev A., Duburs G.
Tetrahedron , 2009
69.
Anodic cyanation of 1-arylpyrroles
Liu W., Ma Y., Zhao Y., Yin Y.
Journal of Heterocyclic Chemistry , 2006
70.
70
N. Bubnov
Biofizika , 1960
71.
71
Yu. A. Shlyapnikov
Vysokomol. Soed. , 1962
72.
72
A. F. Lukovnikov
"Starenie i Stabilizatsiya Polimerov" (Aging arid Stabilisation of Polymers) , 1963
73.
Electrochemical modeling of the dehydrogenation of heterocycles. Oxidation of 3,4-dihydro-2-quinoxalinone derivatives
Sosonkin I.M., Strogov G.N., Charushin V.N., Chupakhin O.N.
Chemistry of Heterocyclic Compounds , 1981
74.
10.1002/1521-3765(20010417)7:8<1759::AID-CHEM17590>3.0.CO;2-F
75.
75
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
76.
Electrochemical Synthesis of Nitroanilines
Gallardo I., Guirado G., Marquet J.
European Journal of Organic Chemistry , 2002
78.
78
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
80.
Lund H., Tegnér C., Takman B.
Acta Chemica Scandinavica , 1957
81.
Svanholm U., Parker V.D., Strand U., Jalonen H., Lüning B., Swahn C.
Acta Chemica Scandinavica , 1973
82.
Reitstöen B., Parker V.D., Lillerud K., Högfeldt E., Spielbüchler P., Pedersen J.B., Krogsgaard-Larsen P.
Acta Chemica Scandinavica , 2008
83.
Reactivity of Aromatic Radical Cations. Rate Constants for Reactions of 9-Phenyl- and 9,10-Diphenylanthracene Radical Cations with Acyclic Amines
Workentin M.S., Johnston L.J., Wayner D.D., Parker V.D.
Journal of the American Chemical Society , 1994
85.
85
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
86.
86
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
87.
Electrosynthesis and electrochemical properties of porphyrin dimers with pyridinium as bridging spacer
Schaming D., Marggi-Poullain S., Ahmed I., Farha R., Goldmann M., Gisselbrecht J., Ruhlmann L.
New Journal of Chemistry , 2011
88.
Stable σH-adducts in the reactions of the acridinium cation with heterocyclic N-nucleophiles
Shchepochkin A.V., Chupakhin O.N., Charushin V.N., Rusinov G.L., Subbotina Y.O., Slepukhin P.A., Budnikova Y.G.
Russian Chemical Bulletin , 2013
89.
89
A. A. Krasnovskii
Izd. Akad. Nauk SSSR, Moscow , 1955
91.
91
L. M. Vorob'eva
Biokhimiya , 1956
97.
Anodic azolation of 1,2- and 1,3-dimethoxybenzenes
Petrosyan V.A., Burasov A.V.
Russian Chemical Bulletin , 2010
98.
Sigacheva Vera Leonidovna, Kokorekin Vladimir Alekseevich, Strelenko Yurii Andreevich, Neverov Sergey Vladimirovich, Petrosyan Vladimir Anushavanovich
Mendeleev Communications , 2012
99.
Oral Azole Drugs as Systemic Antifungal Therapy
Wood A.J., Como J.A., Dismukes W.E.
New England Journal of Medicine , 1994
100.
An Improved and Scalable Process for Celecoxib: A Selective Cyclooxygenase-2 Inhibitor
Reddy A.R., Sampath A., Goverdhan G., Yakambaram B., Mukkanti K., Reddy P.P.
Organic Process Research and Development , 2008
101.
Electrochemical synthesis of a pyridinium-conjugated assembly based on nucleophilic substitution of oligothiophene π-radical cation
Li Y., Kamata K., Kawai T., Abe J., Iyoda T.
Journal of the Chemical Society Perkin Transactions 1 , 2002
103.
Parker V.D., Carnmalm B., Sjöberg B., Karrer P., Shimizu A.
Acta Chemica Scandinavica , 2008
104.
Parker V.D., Nilsson A., Wikander G., Karrer P., Shimizu A.
Acta Chemica Scandinavica , 1970
105.
Hydroxylation and amidation of aromatic carbonyl compounds
So Y., Becker J.Y., Miller L.L.
Journal of the Chemical Society Chemical Communications , 1975
109.
109
F. Ficher
Bull. Soc. chim. France (4) , 1916
111.
10.1002/1521-4109(200108)13:12<1008::AID-ELAN1008>3.0.CO;2-1
113.
Eberson L., Oberrauch E., Schaumburg K., Enzell C.R., Enzell C.R.
Acta Chemica Scandinavica , 1981
114.
Anodic aromatic substitution
Eberson L., Nyberg K.
Accounts of Chemical Research , 1973
115.
Blum Z., Cedheim L., Nyberg K., Hörnfeldt A., Servin R., Sternerup H.
Acta Chemica Scandinavica , 1975
116.
Self-Supported Methoxylation and Acetoxylation Electrosynthesis Using a Simple Thin-Layer Flow Cell
Horii D., Atobe M., Fuchigami T., Marken F.
Journal of the Electrochemical Society , 2006
117.
Burasov Alexander Valeryevich, Petrosyan Vladimir Anushavanovich
Mendeleev Communications , 2008
119.
10.1002/1521-4109(200104)13:6<432::AID-ELAN432>3.0.CO;2-D
120.
Synthesis and evaluation of the antitumor activity of 4,5-diamino-substituted 1,2-benzoquinones
Huang Z.D., Chen Y.N., Menon K., Teicher B.A.
Journal of Medicinal Chemistry , 1993
123.
Estimation of heterogeneous rate constants of reaction of electrochemically generatedo-benzoquinones with various nucleophiles containing thiol group
Fotouhi L., Tammari E., Asadi S., Heravi M.M., Nematollahi D.
International Journal of Chemical Kinetics , 2009
125.
Electrochemical halogenation of organic compounds
Lyalin B.V., Petrosyan V.A.
Russian Journal of Electrochemistry , 2013
130.
130
J. Wiemann
Bull. Soc. chim. France , 1958
131.
131
N. Thooi
Compt. rend. , 1958
132.
132
G. Shima
Kyoto Univ. , 1929