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Metal-free hydroarylation of the side chain carbon-carbon double bond of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles in triflic acid. / Zalivatskaya, Anna S.; Ryabukhin, Dmitry S.; Tarasenko, Marina V.; Ivanov, Alexander Yu; Boyarskaya, Irina A.; Grinenko, Elena V.; Osetrova, Ludmila V.; Kofanov, Eugeniy R.; Vasilyev, Aleksander V.
In:
Beilstein Journal of Organic Chemistry, Vol. 13, 11.05.2017, p. 883-894.
Research output: Contribution to journal › Article › peer-review
Harvard
Zalivatskaya, AS, Ryabukhin, DS, Tarasenko, MV, Ivanov, AY
, Boyarskaya, IA, Grinenko, EV, Osetrova, LV, Kofanov, ER
& Vasilyev, AV 2017, '
Metal-free hydroarylation of the side chain carbon-carbon double bond of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles in triflic acid',
Beilstein Journal of Organic Chemistry, vol. 13, pp. 883-894.
https://doi.org/10.3762/bjoc.13.89,
https://doi.org/10.3762/bjoc.13.89APA
Zalivatskaya, A. S., Ryabukhin, D. S., Tarasenko, M. V., Ivanov, A. Y.
, Boyarskaya, I. A., Grinenko, E. V., Osetrova, L. V., Kofanov, E. R.
, & Vasilyev, A. V. (2017).
Metal-free hydroarylation of the side chain carbon-carbon double bond of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles in triflic acid.
Beilstein Journal of Organic Chemistry,
13, 883-894.
https://doi.org/10.3762/bjoc.13.89,
https://doi.org/10.3762/bjoc.13.89Vancouver
Author
Zalivatskaya, Anna S. ; Ryabukhin, Dmitry S. ; Tarasenko, Marina V. ; Ivanov, Alexander Yu
; Boyarskaya, Irina A. ; Grinenko, Elena V. ; Osetrova, Ludmila V. ; Kofanov, Eugeniy R.
; Vasilyev, Aleksander V. /
Metal-free hydroarylation of the side chain carbon-carbon double bond of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles in triflic acid. In:
Beilstein Journal of Organic Chemistry. 2017 ; Vol. 13. pp. 883-894.
BibTeX
@article{c5b4b42e6a3c4773b5412d198147aa92,
title = "Metal-free hydroarylation of the side chain carbon-carbon double bond of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles in triflic acid",
abstract = "The metal-free reaction of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles with arenes in neat triflic acid (TfOH, CF3SO3H), both under thermal and microwave conditions, leads to 5-(2,2-diarylethyl)-3-aryl-1,2,4-oxadiazoles. The products are formed through the regioselective hydroarylation of the side chain carbon-carbon double bond of the starting oxadiazoles in yields up to 97%. According to NMR data and DFT calculations, N4,C-diprotonated forms of oxadiazoles are the electrophilic intermediates in this reaction.",
keywords = "Friedel-Crafts reaction, Hydroarylation, Oxadiazoles, Superelectrophilic activation, Triflic acid",
author = "Zalivatskaya, {Anna S.} and Ryabukhin, {Dmitry S.} and Tarasenko, {Marina V.} and Ivanov, {Alexander Yu} and Boyarskaya, {Irina A.} and Grinenko, {Elena V.} and Osetrova, {Ludmila V.} and Kofanov, {Eugeniy R.} and Vasilyev, {Aleksander V.}",
note = "Funding Information: This work was supported by the Russian Foundation for Basic Research (grants no. 15-03-02936-a). X-ray studies were performed at the Center for X-ray Diffraction Studies, and spectra of cations in FSO3H at low temperature were obtained at the Center for Magnetic Resonance of Saint Petersburg State University, Saint Petersburg, Russia. Publisher Copyright: {\textcopyright} 2017 Zalivatskaya et al.; licensee Beilstein-Institut. Copyright: Copyright 2017 Elsevier B.V., All rights reserved.",
year = "2017",
month = may,
day = "11",
doi = "10.3762/bjoc.13.89",
language = "English",
volume = "13",
pages = "883--894",
journal = "Beilstein Journal of Organic Chemistry",
issn = "1860-5397",
publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",
}
RIS
TY - JOUR
T1 - Metal-free hydroarylation of the side chain carbon-carbon double bond of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles in triflic acid
AU - Zalivatskaya, Anna S.
AU - Ryabukhin, Dmitry S.
AU - Tarasenko, Marina V.
AU - Ivanov, Alexander Yu
AU - Boyarskaya, Irina A.
AU - Grinenko, Elena V.
AU - Osetrova, Ludmila V.
AU - Kofanov, Eugeniy R.
AU - Vasilyev, Aleksander V.
N1 - Funding Information:
This work was supported by the Russian Foundation for Basic Research (grants no. 15-03-02936-a). X-ray studies were performed at the Center for X-ray Diffraction Studies, and spectra of cations in FSO3H at low temperature were obtained at the Center for Magnetic Resonance of Saint Petersburg State University, Saint Petersburg, Russia.
Publisher Copyright:
© 2017 Zalivatskaya et al.; licensee Beilstein-Institut.
Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.
PY - 2017/5/11
Y1 - 2017/5/11
N2 - The metal-free reaction of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles with arenes in neat triflic acid (TfOH, CF3SO3H), both under thermal and microwave conditions, leads to 5-(2,2-diarylethyl)-3-aryl-1,2,4-oxadiazoles. The products are formed through the regioselective hydroarylation of the side chain carbon-carbon double bond of the starting oxadiazoles in yields up to 97%. According to NMR data and DFT calculations, N4,C-diprotonated forms of oxadiazoles are the electrophilic intermediates in this reaction.
AB - The metal-free reaction of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles with arenes in neat triflic acid (TfOH, CF3SO3H), both under thermal and microwave conditions, leads to 5-(2,2-diarylethyl)-3-aryl-1,2,4-oxadiazoles. The products are formed through the regioselective hydroarylation of the side chain carbon-carbon double bond of the starting oxadiazoles in yields up to 97%. According to NMR data and DFT calculations, N4,C-diprotonated forms of oxadiazoles are the electrophilic intermediates in this reaction.
KW - Friedel-Crafts reaction
KW - Hydroarylation
KW - Oxadiazoles
KW - Superelectrophilic activation
KW - Triflic acid
UR - http://www.scopus.com/inward/record.url?scp=85020550247&partnerID=8YFLogxK
U2 - 10.3762/bjoc.13.89
DO - 10.3762/bjoc.13.89
M3 - Article
VL - 13
SP - 883
EP - 894
JO - Beilstein Journal of Organic Chemistry
JF - Beilstein Journal of Organic Chemistry
SN - 1860-5397
ER -
