Journal
MOLECULES
Volume 27, Issue 12, Pages -Publisher
MDPI
DOI: 10.3390/molecules27123860
Keywords
hypervalent iodine; hydroxy(aryl)iodonium; catalysis; aldoximes; intramolecular cycloaddition; nitrogen heterocycles
Funding
- Russian Science Foundation [RSF-21-73-20031, RSF-16-13-10081-P]
- JSPS Fund for the Promotion of Joint International Research [16KK0199]
- JST CREST
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The intramolecular oxidative cycloaddition reaction of alkyne- or alkene-tethered aldoximes was efficiently catalyzed by hypervalent iodine(III) species, resulting in the formation of polycyclic isoxazole derivatives with yields of up to 94%. The structure of the products was confirmed through various methods, including X-ray crystallography. Mechanistic studies revealed the critical role of hydroxy(aryl)iodonium tosylate as a precatalyst, which is formed from 2-iodobenzoic acid and m-chloroperoxybenzoic acid in the presence of a catalytic amount of p-toluenesulfonic acid.
The intramolecular oxidative cycloaddition reaction of alkyne- or alkene-tethered aldoximes was catalyzed efficiently by hypervalent iodine(III) species to afford the corresponding polycyclic isoxazole derivatives in up to a 94% yield. The structure of the prepared products was confirmed by various methods, including X-ray crystallography. Mechanistic study demonstrated the crucial role of hydroxy(aryl)iodonium tosylate as a precatalyst, which is generated from 2-iodobenzoic acid and m-chloroperoxybenzoic acid in the presence of a catalytic amount of p-toluenesulfonic acid.
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