volume 363 issue 14 pages 3566-3576

Copper‐Catalyzed Selective N‐Arylation of Oxadiazolones by Diaryliodonium Salts

Natalia Soldatova 1, 2, 3, 4
Artem V Semenov 5, 6, 7, 8
Kirill K Geyl 1, 3
Vladislava V Matveevskaya 1
Anna S Konstantinova 10, 11
Mikhail M Korsakov 10, 11
Mekhman S. Yusubov 4
12
 
Department of Solid State Engineering Institute of Chemical Technology Prague 16628 Czech Republic
Publication typeJournal Article
Publication date2021-06-08
scimago Q1
wos Q1
SJR0.930
CiteScore8.0
Impact factor4.0
ISSN16154150, 16154169
General Chemistry
Abstract

Here, we report the method for copper‐catalyzed N‐arylation of diverse oxadiazolones by diaryliodonium salts under mild conditions in high yields (up to 92%) using available CuI as a catalyst. The developed method allows utilizing both symmetric and unsymmetric diaryliodonium salts bearing auxiliary groups such as 2,4,6‐trimethoxyphenyl (TMP). We found that the steric effects in aryl moieties determined the chemoselectivity of N‐ and O‐arylation of the 1,2,4‐oxadiazol‐5(4H)‐ones. Mesityl‐substituted diaryliodonium salts demonstrated the high potential as a selective arylation reagent. The structural study suggests that steric accessibility of N‐atom in 1,2,4‐oxadiazol‐5(4H)‐ones impact to arylation with sterically hindered diaryliodonium salts. The synthetic application of proposed method was also demonstrated on selective arylation of 1,3,4‐oxadiazol‐2(3H)‐ones and 1,2,4‐oxadiazole‐5‐thiol.

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Soldatova N. et al. Copper‐Catalyzed Selective N‐Arylation of Oxadiazolones by Diaryliodonium Salts // Advanced Synthesis and Catalysis. 2021. Vol. 363. No. 14. pp. 3566-3576.
GOST all authors (up to 50) Copy
Soldatova N., Semenov A. V., Geyl K. K., Matveevskaya V. V., Baykov S. V., Shetnev A. A., Konstantinova A. S., Korsakov M. M., S. Yusubov M., Yusubov M. S., Postnikov P. S. Copper‐Catalyzed Selective N‐Arylation of Oxadiazolones by Diaryliodonium Salts // Advanced Synthesis and Catalysis. 2021. Vol. 363. No. 14. pp. 3566-3576.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1002/adsc.202100426
UR - https://onlinelibrary.wiley.com/doi/10.1002/adsc.202100426
TI - Copper‐Catalyzed Selective N‐Arylation of Oxadiazolones by Diaryliodonium Salts
T2 - Advanced Synthesis and Catalysis
AU - Soldatova, Natalia
AU - Semenov, Artem V
AU - Geyl, Kirill K
AU - Matveevskaya, Vladislava V
AU - Baykov, Sergey V
AU - Shetnev, Anton A
AU - Konstantinova, Anna S
AU - Korsakov, Mikhail M
AU - S. Yusubov, Mekhman
AU - Yusubov, Mekhman S.
AU - Postnikov, Pavel S.
PY - 2021
DA - 2021/06/08
PB - Wiley
SP - 3566-3576
IS - 14
VL - 363
SN - 1615-4150
SN - 1615-4169
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2021_Soldatova,
author = {Natalia Soldatova and Artem V Semenov and Kirill K Geyl and Vladislava V Matveevskaya and Sergey V Baykov and Anton A Shetnev and Anna S Konstantinova and Mikhail M Korsakov and Mekhman S. Yusubov and Mekhman S. Yusubov and Pavel S. Postnikov},
title = {Copper‐Catalyzed Selective N‐Arylation of Oxadiazolones by Diaryliodonium Salts},
journal = {Advanced Synthesis and Catalysis},
year = {2021},
volume = {363},
publisher = {Wiley},
month = {jun},
url = {https://onlinelibrary.wiley.com/doi/10.1002/adsc.202100426},
number = {14},
pages = {3566--3576},
doi = {10.1002/adsc.202100426}
}
MLA
Cite this
MLA Copy
Soldatova, Natalia, et al. “Copper‐Catalyzed Selective N‐Arylation of Oxadiazolones by Diaryliodonium Salts.” Advanced Synthesis and Catalysis, vol. 363, no. 14, Jun. 2021, pp. 3566-3576. https://onlinelibrary.wiley.com/doi/10.1002/adsc.202100426.