期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 363, 期 14, 页码 3566-3576出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202100426
关键词
Iodonium salts; Arylation; Amides; Heterocycles; Chemoselectivity
资金
- Russian Science Foundation [19-73-00007]
- Ministry of Science and Higher Education of Russian Federation [2020-220-08-8827]
- Russian Science Foundation [19-73-00007] Funding Source: Russian Science Foundation
A method for copper-catalyzed N-arylation of diverse oxadiazolones using diaryliodonium salts has been reported with high yields up to 92%. It was found that the steric effects in aryl moieties determined the chemoselectivity of arylations. Mesityl-substituted diaryliodonium salts demonstrated high potential as selective arylation reagents.
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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