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Upstream product

• 3235-02-7 p-methylbenzaldehyde oxime 
• 31827-28-8 4,5-dihydro-3-(p-tolyl)-1,2,4-oxadiazol-5-one 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 16668-99-8 bis(phenyl)iodonium trifluoroacetate 
• 144930-50-7 mesityl(phenyl)iodonium triflouromethanesulfonate 
• 936326-60-2 phenyl(2,4,6-trimethoxyphenyl)iodonium 4-methylbenzenesulfonate 
• 98-80-6 phenylboronic acid 
• 591-50-4 iodobenzene 
• 19227-13-5 p-toluamidoxime 
• 1483-73-4 diphenyliodonium bromide 
• 104-87-0 4-methyl-benzaldehyde 
• 36288-37-6 N-hydroxy-4-methylbenzenecarboximidoyl chloride 

Relevant academic research and scientific papers

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

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.).

Tuning chemoselectivity in: O -/ N -arylation of 3-aryl-1,2,4-oxadiazolones with ortho -(trimethylsilyl)phenyl triflates via aryne insertion

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.

Unexpected C-C bond cleavage: Synthesis of 1,2,4-oxadiazol-5-ones from amidoximes with pentafluorophenyl or trifluoromethyl anion acting as leaving group

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.