Premium
Copper‐Catalyzed Selective N‐Arylation of Oxadiazolones by Diaryliodonium Salts
Author(s) -
Soldatova Natalia S.,
Semenov Artem V.,
Geyl Kirill K.,
Baykov Sergey V.,
Shetnev Anton A.,
Konstantinova Anna S.,
Korsakov Mikhail M.,
Yusubov Mekhman S.,
Postnikov Pavel S.
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100426
Subject(s) - chemistry , steric effects , chemoselectivity , reagent , catalysis , aryl , copper , combinatorial chemistry , organic chemistry , alkyl
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(4 H )‐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(4 H )‐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(3 H )‐ones and 1,2,4‐oxadiazole‐5‐thiol.