Journal of Organic Chemistry, volume 85, issue 5, pages 3160-3173
Ullmann-type C-Se Cross-Coupling in the Hydantoin Family: Synthesis, Mechanistic Studies, and Tests of Biological Activity
Vyhivskyi Oleksandr
1
,
Laikov Dimitri
1
,
Finko A V
1
,
Skvortsov Dmitry
1, 2
,
Zhirkina Irina V
1
,
Тафеенко В. А.
1
,
Zyk Nikolay V.
1
,
Majouga Alexander G.
1, 3, 4
,
3
National University of Science and Technology, Leninskii pr., 4, Moscow 119049, Russia
|
Publication type: Journal Article
Publication date: 2020-01-16
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
An attractive strategy for C-Se bond formation by an Ullmann-type copper(I) promoted cross-coupling is developed. A wide range of aryliodides react with various disubstituted 2-selenohydantoins under mild conditions and provides Se-arylated imidazolines in moderate to high yields. Computational mechanistic studies show the oxidative addition/intramolecular reductive elimination likely to be the lowest-energy pathway. Cytotoxic activity of all 55 reaction products has been tested in vitro against MCF7 and A549 cancer cell lines with VA13 and MCF10a control cells.
Citations by journals
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1
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Bioorganic Chemistry
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Bioorganic Chemistry
1 publication, 16.67%
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Journal of Chemical Physics
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Journal of Chemical Physics
1 publication, 16.67%
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Russian Chemical Bulletin
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Russian Chemical Bulletin
1 publication, 16.67%
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RSC Advances
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RSC Advances
1 publication, 16.67%
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Chemistry - A European Journal
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Chemistry - A European Journal
1 publication, 16.67%
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Molecular Catalysis
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Molecular Catalysis
1 publication, 16.67%
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1
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Citations by publishers
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1
2
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Elsevier
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Elsevier
2 publications, 33.33%
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American Institute of Physics (AIP)
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American Institute of Physics (AIP)
1 publication, 16.67%
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Springer Nature
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Springer Nature
1 publication, 16.67%
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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
1 publication, 16.67%
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Wiley
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Wiley
1 publication, 16.67%
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1
2
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- We do not take into account publications that without a DOI.
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Vyhivskyi O. et al. Ullmann-type C-Se Cross-Coupling in the Hydantoin Family: Synthesis, Mechanistic Studies, and Tests of Biological Activity // Journal of Organic Chemistry. 2020. Vol. 85. No. 5. pp. 3160-3173.
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Vyhivskyi O., Laikov D., Finko A. V., Skvortsov D., Zhirkina I. V., Тафеенко В. А., Zyk N. V., Majouga A. G., Beloglazkina E. K. Ullmann-type C-Se Cross-Coupling in the Hydantoin Family: Synthesis, Mechanistic Studies, and Tests of Biological Activity // Journal of Organic Chemistry. 2020. Vol. 85. No. 5. pp. 3160-3173.
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TY - JOUR
DO - 10.1021/acs.joc.9b03045
UR - https://doi.org/10.1021%2Facs.joc.9b03045
TI - Ullmann-type C-Se Cross-Coupling in the Hydantoin Family: Synthesis, Mechanistic Studies, and Tests of Biological Activity
T2 - Journal of Organic Chemistry
AU - Vyhivskyi, Oleksandr
AU - Zhirkina, Irina V
AU - Zyk, Nikolay V.
AU - Laikov, Dimitri
AU - Finko, A V
AU - Majouga, Alexander G.
AU - Skvortsov, Dmitry
AU - Тафеенко, В. А.
AU - Beloglazkina, Elena K.
PY - 2020
DA - 2020/01/16 00:00:00
PB - American Chemical Society (ACS)
SP - 3160-3173
IS - 5
VL - 85
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2020_Vyhivskyi,
author = {Oleksandr Vyhivskyi and Irina V Zhirkina and Nikolay V. Zyk and Dimitri Laikov and A V Finko and Alexander G. Majouga and Dmitry Skvortsov and В. А. Тафеенко and Elena K. Beloglazkina},
title = {Ullmann-type C-Se Cross-Coupling in the Hydantoin Family: Synthesis, Mechanistic Studies, and Tests of Biological Activity},
journal = {Journal of Organic Chemistry},
year = {2020},
volume = {85},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021%2Facs.joc.9b03045},
number = {5},
pages = {3160--3173},
doi = {10.1021/acs.joc.9b03045}
}
Cite this
MLA
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Vyhivskyi, Oleksandr, et al. “Ullmann-type C-Se Cross-Coupling in the Hydantoin Family: Synthesis, Mechanistic Studies, and Tests of Biological Activity.” Journal of Organic Chemistry, vol. 85, no. 5, Jan. 2020, pp. 3160-3173. https://doi.org/10.1021%2Facs.joc.9b03045.