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C(sp2) -- H functionalization of aldimines and related compounds: advances and prospects

Alexey Alexandrovich Akulov 1, 2
Alexey Alexandrovich Akulov
, 
Mikhail Viktorovich Varaksin 1, 2
Mikhail Viktorovich Varaksin
, 
Valery Nikolaevich Charushin
, 
Oleg Nikolaevich Chupakhin 1, 2
Oleg Nikolaevich Chupakhin
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
Published 30 November 2020
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Akulov A. A. et al. C(sp2) -- H functionalization of aldimines and related compounds: advances and prospects // Russian Chemical Reviews. 2020. Vol. 90. No. 3. pp. 374-394.
GOST all authors (up to 50)
Akulov A. A., Varaksin M. V., Charushin V. N., Chupakhin O. N. C(sp2) -- H functionalization of aldimines and related compounds: advances and prospects // Russian Chemical Reviews. 2020. Vol. 90. No. 3. pp. 374-394.
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TY - JOUR
DO - 10.1070/RCR4978
UR - https://rcr.colab.ws/publications/10.1070/RCR4978
TI - C(sp2) -- H functionalization of aldimines and related compounds: advances and prospects
T2 - Russian Chemical Reviews
AU - Akulov, Alexey Alexandrovich
AU - Varaksin, Mikhail Viktorovich
AU - Charushin, Valery Nikolaevich
AU - Chupakhin, Oleg Nikolaevich
PY - 2020
DA - 2020/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 374-394
IS - 3
VL - 90
ER -
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@article{2020_Akulov,
author = {Alexey Alexandrovich Akulov and Mikhail Viktorovich Varaksin and Valery Nikolaevich Charushin and Oleg Nikolaevich Chupakhin},
title = {C(sp2) -- H functionalization of aldimines and related compounds: advances and prospects},
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/RCR4978},
number = {3},
pages = {374--394},
doi = {10.1070/RCR4978}
}
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Cite this
MLA
Akulov, Alexey Alexandrovich, et al. “C(sp2) -- H functionalization of aldimines and related compounds: advances and prospects.” Russian Chemical Reviews, vol. 90, no. 3, Nov. 2020, pp. 374-394. https://rcr.colab.ws/publications/10.1070/RCR4978.
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Keywords

AZOMETHINES
C–H activation
HYDRAZONES
imines
NITRONES
OXIMES
SCHIFF BASES

Abstract

This is the first systematic review of the most relevant approaches to direct C(sp2) -- H bond functionalization of azomethine derivatives. The scope of the applicability of various transformations is analyzed. The review assesses prospects of the application of this functionalization strategy in the multistep synthesis of valuable compounds for use in medicinal chemistry, materials science and related areas.

The bibliography includes 124 references.

Funders

Russian Foundation for Basic Research
19-13-50193

References

4.
rcr_90_3_374bib4
Bidusenko
2018
5.
rcr_90_3_374bib5
Schmidt
2019
6.
Catalyst- and Solvent-Free Synthesis of α-Amino Polyfluoroalkylphosphonates from Bis(fluoroalkyl) Phosphonates and Aldimines
Trofimov B.A., Arbuzova S.N., Gusarova N.K., Kazantseva T.I., Verkhoturova S.I., Zinchenko S.V., Kolyvanov N.A.
Synthesis , 2020
8.
1,3-Dipolar cycloadditions of azomethine imines
Nájera C., Sansano J.M., Yus M.
Organic and Biomolecular Chemistry , 2015
9.
Hydrazones as substrates for cycloaddition reactions
Belskaya N.P., Eliseeva A.I., Bakulev V.A.
Russian Chemical Reviews , 2015
10.
Synthesis and (3+2) cycloaddition reactions of N,N ʹ- and C,N-cyclic azomethine imines
Belskaya N.P., Bakulev V.A., Fan Z.
Chemistry of Heterocyclic Compounds , 2016
13.
rcr_90_3_374bib13
Dixneuf
2016
14.
rcr_90_3_374bib14
Li
2015
15.
rcr_90_3_374bib15
Brehme
2007
16.
rcr_90_3_374bib16
Hickmott
1994
17.
rcr_90_3_374bib17
Alt
1988
18.
The Enamine Alkylation and Acylation of Carbonyl Compounds
Stork G., Brizzolara A., Landesman H., Szmuszkovicz J., Terrell R.
Journal of the American Chemical Society , 1963
19.
rcr_90_3_374bib19
Szmuszkovicz
Advances in Organic Chemistry , 1963
20.
Aza‐enamine Vilsmeier‐Formylierung von Aldehydhydrazonen
22.
Enamin-analogue reaktionen von aldehyd-N,N-dimethylhydrazonen.
24.
Electrophilic substitution at azomethine carbon atoms. Reaction of aromatic aldehyde hydrazones with trifluoroacetic anhydride
Kamitori Y., Hojo M., Masuda R., Fujitani T., Ohara S., Yokoyama T.
Journal of Organic Chemistry , 1988
25.
Copper-Catalyzed Trifluoromethylation ofN,N-Dialkylhydrazones
Pair E., Monteiro N., Bouyssi D., Baudoin O.
Angewandte Chemie - International Edition , 2013
28.
rcr_90_3_374bib28
Zhang
Org. Biomol. Chem. , 2016
29.
Palladium-Catalyzed C(sp2 )−H Alkylation of Aldehyde-Derived Hydrazones with Functionalized Difluoromethyl Bromides
Prieto A., Melot R., Bouyssi D., Monteiro N.
Angewandte Chemie - International Edition , 2015
32.
Gold-Catalyzed Highly Selective Photoredox C(sp2 )−H Difluoroalkylation and Perfluoroalkylation of Hydrazones
Xie J., Zhang T., Chen F., Mehrkens N., Rominger F., Rudolph M., Hashmi A.S.
Angewandte Chemie - International Edition , 2016
33.
Visible-Light Photoredox-Catalyzed C−H Difluoroalkylation of Hydrazones through an Aminyl Radical/Polar Mechanism
Xu P., Wang G., Zhu Y., Li W., Cheng Y., Li S., Zhu C.
Angewandte Chemie - International Edition , 2015
35.
rcr_90_3_374bib35
Zhu
RSC Adv. , 2017
36.
Oxidative C(sp2)–H Phosphonation of Aldehyde Hydrazones
Xu P., Wu Z., Zhou N., Zhu C.
Organic Letters , 2016
38.
C(sp2)–H functionalization of aldehyde-derived hydrazones via a radical process
Xu X., Zhang J., Xia H., Wu J.
Organic and Biomolecular Chemistry , 2018
39.
Photoredox Catalysis for Building C-C Bonds from C(sp2)-H Bonds.
40.
Copper-Catalyzed Transformation of Hydrazones into Halogenated Azabutadienes, Versatile Building Blocks for Organic Synthesis
Nenajdenko V.G., Shastin A.V., Gorbachev V.M., Shorunov S.V., Muzalevskiy V.M., Lukianova A.I., Dorovatovskii P.V., Khrustalev V.N.
ACS Catalysis , 2016
41.
2H-Bis-1,2,3-triazolo-isoquinoline: Design, Synthesis, and Photophysical Study
Tsyrenova B., Khrustalev V., Nenajdenko V.
Journal of Organic Chemistry , 2020
42.
Synthesis of a New Family of 1,1-Diazidoethenes: One-Pot Construction of 4-Azido-1,2,3-triazoles via Nitrene Cyclization.
Shastin A.V., Tsyrenova B.D., Sergeev P.G., Roznyatovsky V.A., Smolyar I.V., Khrustalev V.N., Nenajdenko V.G.
Organic Letters , 2018
44.
rcr_90_3_374bib44
Shastin
2018
45.
rcr_90_3_374bib45
Sergeev
2020
51.
rcr_90_3_374bib51
Park
2005
52.
Rh(I)-Catalyzed Arylation of Heterocycles via C−H Bond Activation:  Expanded Scope through Mechanistic Insight
Lewis J.C., Berman A.M., Bergman R.G., Ellman J.A.
Journal of the American Chemical Society , 2008
59.
The First Example of Palladium(II)-Catalyzed Oxidative C–N Cross Coupling of 2H-Imidazole 1-Oxide with Azoles
Akulov A.A., Varaksin M.V., Charushin V.N., Chupakhin O.N.
Chemistry of Heterocyclic Compounds , 2019
62.
Straightforward synthesis of enantiopure 2-aminomethyl and 2-hydroxymethyl pyrrolidines with complete stereocontrol
Marradi M., Cicchi S., Ignacio Delso J., Rosi L., Tejero T., Merino P., Goti A.
Tetrahedron Letters , 2005
63.
Metal-free C–H functionalization of 2H-imidazole 1-oxides with pyrrolyl fragments in the design of novel azaheterocyclic ensembles
Varaksin M., Moseev T., Chupakhin O., Charushin V., Trofimov B.
Organic and Biomolecular Chemistry , 2017
68.
α-Organoelement Nitrones:  Synthesis, Properties, and IR and13C NMR Spectral and X-ray Structural Characterization
Voinov M.A., Shevelev T.G., Rybalova T.V., Gatilov Y.V., Pervukhina N.V., Burdukov A.B., Grigor'ev I.A.
Organometallics , 2007
69.
Direct C–C Coupling of Cyclic Aldonitrones with 1,2,4-Triazines Using S N H Reactions
Varaksin M.V., Utepova I.A., Chupakhin O.N.
Chemistry of Heterocyclic Compounds , 2012
71.
C(sp2)–H functionalization in non-aromatic azomethine-based heterocycles
Akulov A.A., Varaksin M.V., Mampuys P., Charushin V.N., Chupakhin O.N., Maes B.U.
Organic and Biomolecular Chemistry , 2021
72.
rcr_90_3_374bib72
Powell
2009
77.
Progress in hydroformylation and carbonylation
Beller M., Cornils B., Frohning C.D., Kohlpaintner C.W.
Journal of Molecular Catalysis A Chemical , 1995
78.
[2+2+2] Cycloaddition Reactions Catalyzed by Transition Metal Complexes
Chopade P., Louie J.
Advanced Synthesis and Catalysis , 2006
79.
rcr_90_3_374bib79
Hess
2008
80.
Low-valent cobalt catalysis: new opportunities for C-H functionalization.
Gao K., Yoshikai N.
Accounts of Chemical Research , 2014
89.
Copper-Catalyzed CH Oxidation/Cross-Coupling of α-Amino Carbonyl Compounds
Wu J., Song R., Wang Z., Huang X., Xie Y., Li J.
Angewandte Chemie - International Edition , 2012
91.
rcr_90_3_374bib91
Caesar
Clin. Sci. , 1961
92.
Cyanine dye labeling reagents for sulfhydryl groups.
Ernst L.A., Gupta R.K., Mujumdar R.B., Waggoner A.S.
Cytometry , 1989
93.
An Air-Stable Oxyallyl Radical Cation
Martin D., Moore C.E., Rheingold A.L., Bertrand G.
Angewandte Chemie - International Edition , 2013
94.
A cyclic diaminocarbene with a pyramidalized nitrogen atom: a stable N-heterocyclic carbene with enhanced electrophilicity.
Martin D., Lassauque N., Donnadieu B., Bertrand G.
Angewandte Chemie - International Edition , 2012
96.
Bredt's rule
Buchanan G.L.
Chemical Society Reviews , 1974
97.
Crystalline Monomeric Allenyl/Propargyl Radical
Hansmann M.M., Melaimi M., Bertrand G.
Journal of the American Chemical Society , 2017
100.
Isolation of cationic and neutral (allenylidene)(carbene) and bis(allenylidene)gold complexes
Jin L., Melaimi M., Kostenko A., Karni M., Apeloig Y., Moore C.E., Rheingold A.L., Bertrand G.
Chemical Science , 2016
101.
Enantioselective N‐Heterocyclic Carbene Catalysis that Exploits Imine Umpolung
Fernando J.E., Nakano Y., Zhang C., Lupton D.W.
Angewandte Chemie - International Edition , 2019
102.
Transition-Metal-Free Superbase-Catalyzed C–H Vinylation of Aldimines with Acetylenes to 1-Azadienes
Schmidt E.Y., Bidusenko I.A., Protsuk N.I., Demyanov Y.V., Ushakov I.A., Vashchenko A.V., Trofimov B.A.
Journal of Organic Chemistry , 2020
103.
KOBut/DMSO-Mediated α-C–H Vinylation of N-Benzyl Ketimines with Acetylene Gas: Stereoselective Synthesis of (E,Z)-2-Azadienes
Bidusenko I.A., Schmidt E.Y., Protsuk N.I., Ushakov I.A., Vashchenko A.V., Afonin A.V., Trofimov B.A.
Organic Letters , 2020
104.
Synthesis, optical and nonlinear optical properties of new pyrazoline derivatives
Mysliwiec J., Szukalski A., Sznitko L., Miniewicz A., Haupa K., Zygadlo K., Matczyszyn K., Olesiak-Banska J., Samoc M.
Dyes and Pigments , 2014
106.
Ion-pairing catalysis in the enantioselective addition of hydrazones to N-acyldihydropyrrole derivatives
Zabaleta N., Uria U., Reyes E., Carrillo L., Vicario J.L.
Chemical Communications , 2018
107.
rcr_90_3_374bib107
Chen
2018
111.
rcr_90_3_374bib111
Petunin
2018
112.
H2O-controlled selective thiocyanation and alkenylation of ketene dithioacetals under electrochemical oxidation
Wen J., Zhang L., Yang X., Niu C., Wang S., Wei W., Sun X., Yang J., Wang H.
Green Chemistry , 2019
115.
From Phenylhydrazone to 1 H ‐1,2,4‐Triazoles via Nitrification, Reduction and Cyclization
Hao L., Wang G., Sun J., Xu J., Li H., Duan G., Xia C., Zhang P.
Advanced Synthesis and Catalysis , 2020
119.
rcr_90_3_374bib119
Grigor’ev
2008
120.
From Natural Product‐Inspired Pyrrolidine Scaffolds to the Development of New Human Golgi α‐Mannosidase II Inhibitors
Cheng T.R., Chan T., Tsou E., Chang S., Yun W., Yang P., Wu Y., Cheng W.
Chemistry - An Asian Journal , 2013
121.
Structure, mechanism and inhibition of Golgi α-mannosidase II
Rose D.R.
Current Opinion in Structural Biology , 2012
124.
rcr_90_3_374bib124
Zhang
2019