Ullmann-type C-Se Cross-Coupling in the Hydantoin Family: Synthesis, Mechanistic Studies, and Tests of Biological Activity
Oleksandr Vyhivskyi
1
,
Dimitri Laikov
1
,
A V Finko
1
,
Dmitry Skvortsov
1, 2
,
Dmitry A. Skvortsov
1, 2
,
Irina V Zhirkina
1
,
В. А. Тафеенко
1
,
Victor A. Tafeenko
1
,
Nikolay V. Zyk
1
,
Alexander G. Majouga
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
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
31944122
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.
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13
Total citations:
13
Citations from 2024:
8
(61%)
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MLA
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GOST
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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.
GOST all authors (up to 50)
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Vyhivskyi O., Laikov D., Finko A. V., Skvortsov D., Skvortsov D. A., Zhirkina I. V., Тафеенко В. А., Tafeenko V. A., 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.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.joc.9b03045
UR - https://pubs.acs.org/doi/10.1021/acs.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 - Laikov, Dimitri
AU - Finko, A V
AU - Skvortsov, Dmitry
AU - Skvortsov, Dmitry A.
AU - Zhirkina, Irina V
AU - Тафеенко, В. А.
AU - Tafeenko, Victor A.
AU - Zyk, Nikolay V.
AU - Majouga, Alexander G.
AU - Beloglazkina, Elena K.
PY - 2020
DA - 2020/01/16
PB - American Chemical Society (ACS)
SP - 3160-3173
IS - 5
VL - 85
PMID - 31944122
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2020_Vyhivskyi,
author = {Oleksandr Vyhivskyi and Dimitri Laikov and A V Finko and Dmitry Skvortsov and Dmitry A. Skvortsov and Irina V Zhirkina and В. А. Тафеенко and Victor A. Tafeenko and Nikolay V. Zyk and Alexander G. Majouga 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://pubs.acs.org/doi/10.1021/acs.joc.9b03045},
number = {5},
pages = {3160--3173},
doi = {10.1021/acs.joc.9b03045}
}
Cite this
MLA
Copy
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://pubs.acs.org/doi/10.1021/acs.joc.9b03045.