Advanced Synthesis and Catalysis, volume 363, issue 14, pages 3566-3576

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

Semenov Artem V 3, 4
Matveevskaya Vladislava V 1
Konstantinova Anna S 6
Korsakov Mikhail M 6
Publication typeJournal Article
Publication date2021-06-08
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor5.4
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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GOST Copy
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., Shetnev A. A., Konstantinova A. S., Korsakov M. M., S. Yusubov M., 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://doi.org/10.1002%2Fadsc.202100426
TI - Copper‐Catalyzed Selective N‐Arylation of Oxadiazolones by Diaryliodonium Salts
T2 - Advanced Synthesis and Catalysis
AU - Semenov, Artem V
AU - Geyl, Kirill K
AU - Konstantinova, Anna S
AU - Korsakov, Mikhail M
AU - Soldatova, Natalia
AU - Matveevskaya, Vladislava V
AU - Shetnev, Anton A
AU - S. Yusubov, Mekhman
AU - Postnikov, Pavel S.
PY - 2021
DA - 2021/06/08 00:00:00
PB - Wiley
SP - 3566-3576
IS - 14
VL - 363
SN - 1615-4150
SN - 1615-4169
ER -
BibTex |
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BibTex Copy
@article{2021_Soldatova
author = {Artem V Semenov and Kirill K Geyl and Anna S Konstantinova and Mikhail M Korsakov and Natalia Soldatova and Vladislava V Matveevskaya and Anton A Shetnev 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://doi.org/10.1002%2Fadsc.202100426},
number = {14},
pages = {3566--3576},
doi = {10.1002/adsc.202100426}
}
MLA
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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://doi.org/10.1002%2Fadsc.202100426.
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