Hypervalent iodine-induced formation of 3,5-disubstituted isoxazoles via [3 + 2] cycloaddition of diynes with aldoximes
A direct and efficient synthetic route for [3 + 2] cycloaddition of diynes with aldoximes induced by hypervalent iodine has been described, thus providing 3,5-disubstituted isoxazoles in moderate to good yields with high regioselectivity at room temperature. This transformation was carried out in th...
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| Published in | Monatshefte für Chemie Vol. 148; no. 6; pp. 1109 - 1116 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Vienna
Springer Vienna
01.06.2017
Springer Nature Springer Nature B.V |
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| Abstract | A direct and efficient synthetic route for [3 + 2] cycloaddition of diynes with aldoximes induced by hypervalent iodine has been described, thus providing 3,5-disubstituted isoxazoles in moderate to good yields with high regioselectivity at room temperature. This transformation was carried out in the presence of [bis(trifluoroacetoxy)iodo]benzene as a promoter and demonstrated high levels of functional-group tolerance.
Graphical abstract |
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| AbstractList | A direct and efficient synthetic route for [3 + 2] cycloaddition of diynes with aldoximes induced by hypervalent iodine has been described, thus providing 3,5-disubstituted isoxazoles in moderate to good yields with high regioselectivity at room temperature. This transformation was carried out in the presence of [bis(trifluoroacetoxy)iodo]benzene as a promoter and demonstrated high levels of functional-group tolerance. A direct and efficient synthetic route for [3 + 2] cycloaddition of diynes with aldoximes induced by hypervalent iodine has been described, thus providing 3,5-disubstituted isoxazoles in moderate to good yields with high regioselectivity at room temperature. This transformation was carried out in the presence of [bis(trifluoroacetoxy)iodo]benzene as a promoter and demonstrated high levels of functional-group tolerance. Graphical abstract A direct and efficient synthetic route for [3 + 2] cycloaddition of diynes with aldoximes induced by hypervalent iodine has been described, thus providing 3,5-disubstituted isoxazoles in moderate to good yields with high regioselectivity at room temperature. This transformation was carried out in the presence of [bis(trifluoroacetoxy)iodo]benzene as a promoter and demonstrated high levels of functional-group tolerance. Graphical abstract |
| Author | Chen, San-Xu Xu, Fen Zhu, Ying-Ying Kang, Wei-Fen Kong, Yue-Jie Fang, Shao-Ming Wang, Xiao-Ning |
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| Keywords | Isoxazoles Oxides Cycloadditions Alkynes OXIMES ANALOGS ARENES GENERATION NITRILE OXIDE CYCLOADDITIONS INHIBITORS CATALYST DERIVATIVES |
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| Snippet | A direct and efficient synthetic route for [3 + 2] cycloaddition of diynes with aldoximes induced by hypervalent iodine has been described, thus providing... A direct and efficient synthetic route for [3 + 2] cycloaddition of diynes with aldoximes induced by hypervalent iodine has been described, thus providing... |
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| SubjectTerms | Analytical Chemistry Benzene Chemistry Chemistry and Materials Science Chemistry, Multidisciplinary Chemistry/Food Science Cycloaddition Inorganic Chemistry Iodine Organic Chemistry Original Paper Physical Chemistry Physical Sciences Regioselectivity Room temperature Science & Technology Theoretical and Computational Chemistry |
| Title | Hypervalent iodine-induced formation of 3,5-disubstituted isoxazoles via [3 + 2] cycloaddition of diynes with aldoximes |
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