期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 82, 期 12, 页码 6358-6365出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00946
关键词
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资金
- Department of Science and Technology (DST), New Delhi [SB/S1/OC-53/2013]
- Council of Scientific and Industrial Research (CSIR) [02(0096)/12/EMR-II]
- [MHRD: 5-5/2014-TS-VII]
A sequential construction of C-C, C-O, C=N, and C=O bonds from alkenes leading to the direct synthesis of isoxazolines in the presence of tert-butyl nitrite, quinoline, and the Sc(OTf)(3) catalyst in DCE at 80 C-omicron has been accomplished. An unprecedented three consecutive C-H functionalizations of two styrenes are involved in this isoxazoline synthesis. In this radical-mediated reaction, one-half of the aryl alkene is converted into an intermediate 2-nitroketone, which serves as a 1,3-dipolarophile and undergoes cycloaddition with the other half of the unreacted aromatic terminal alkene. The use of an alkyne in lieu of an alkene leads to the formation of isoxazole under identical reaction conditions.
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