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Copper-Catalyzed Selective Arylation of Oxadiazolones by Diaryliodonium Salts

preprint
submitted on 03.04.2021, 10:26 and posted on 05.04.2021, 13:56 by Natalia Soldatova, Artem Semenov, Kirill Geyl, Sergey Baykov, Anton Shetnev, Anna Konstantinova, Mikhail Korsakov, Mekhman Yusubov, Pavel Postnikov
The direct N-arylation of cyclic amides can be considered a pivotal issue for modern organic chemistry. Here, we report the method for copper-catalyzed N-arylation of diverse oxadiazolones by diaryliodonium salts in mild conditions in high yields (up to 92%) using available CuI as a catalyst. The developed method allows to efficiently utilize both symmetric and unsymmetric diaryliodonium salts bearing auxiliary groups such as 2,4,6-trimethoxyphenyl (TMP). The evaluation of steric effects in aryl moieties to the chemoselectivity of N- and O-arylation of the 1,2,4-oxadiazol-5(4H)-ones exhibited the high potential of mesityl-substituted diaryliodonium salts 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.

Funding

Russian Science Foundation (№ 19-73-00007)

Ministry of Science and Higher Education of Russian Federation ("Mega-grant" project, application number 2020-220-08-8827)

History

Email Address of Submitting Author

postnikov@tpu.ru

Institution

Tomsk Polytechnic University

Country

Russian Federation

ORCID For Submitting Author

0000-0001-9713-1290

Declaration of Conflict of Interest

The authors declare the absence of conflict of interests.

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