通过醛肟的分子内氧化环加成反应高效催化合成稠合异恶唑衍生物。
Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes.
机构信息
Research School of Chemistry and Applied Biomedical Sciences, Tomsk Polytechnic University, 634050 Tomsk, Russia.
Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russia.
出版信息
Molecules. 2022 Jun 16;27(12):3860. doi: 10.3390/molecules27123860.
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 -chloroperoxybenzoic acid in the presence of a catalytic amount of -toluenesulfonic acid.
炔烃或烯烃键合的醛肟的分子内氧化环加成反应被高价碘（III）物种高效催化，以高达 94%的收率得到相应的多环异唑衍生物。通过各种方法，包括 X 射线晶体学，确定了所制备产物的结构。机理研究表明，对甲苯磺酸作为一种前催化剂的羟（芳基）碘𬭩对甲苯磺酸盐的关键作用，其在催化量的对甲苯磺酸存在下由 2-碘苯甲酸和 -氯过氧苯甲酸生成。
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