- Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts
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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. (Figure presented.).
- 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.
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p. 3566 - 3576
(2021/06/16)
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- Tuning chemoselectivity in: O -/ N -arylation of 3-aryl-1,2,4-oxadiazolones with ortho -(trimethylsilyl)phenyl triflates via aryne insertion
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Herein, we first describe finely tunable chemoselectivity in arylation of 3-aryl-1,2,4-oxadiazolones with ortho-(trimethylsilyl)phenyl triflates, including O-arylation enabled by catalytic amount of silver nitrate and metal-free N-arylation. Both the arylation reactions can tolerate a series of functional groups, and afford the corresponding products in moderate to good yields.
- Zhou, Lijing,Li, Hongji,Zhang, Wenge,Wang, Lei
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supporting information
p. 4822 - 4825
(2018/05/23)
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- Unexpected C-C bond cleavage: Synthesis of 1,2,4-oxadiazol-5-ones from amidoximes with pentafluorophenyl or trifluoromethyl anion acting as leaving group
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An unexpected C-C bond cleavage has been observed on pentafluorobenzoylamidoximes under mild basic conditions. This observation has been exploited to develop a new synthesis of 1,2,4-oxadiazol-5-ones from amidoximes using pentafluorobenzoyl chloride or trifluoroacetic anhydride (TFAA) as a double acylating agent. The pentafluorophenyl anion and the trifluoromethyl anion acted as leaving groups in this transformation.
- Gerfaud, Thibaud,Wei, Hai-Long,Neuville, Luc,Zhu, Jieping
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p. 6172 - 6175
(2012/01/03)
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