期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 13, 期 17, 页码 4828-4832出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ob00337g
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资金
- CSIR, New Delhi, India
- IIT Ropar
- UGC, New Delhi
A mild, convenient and transition metal free methodology for oxidative ipso nitration of diversely functionalized organoboronic acids, including heteroaryl- and alkylboronic acids, has been developed at ambient temperature using a combination of [bis-(trifluoroacetoxy)]iodobenzene (PIFA) - N-bromosuccinimide (NBS) and sodium nitrite as the nitro source. It is anticipated that the reaction proceeds through in situ generation of NO2 and O-centred organoboronic acid radicals followed by the formation of an O-N bond via combination of the said radicals. Finally transfer of the NO2 group to the aryl moiety occurs through 1,3-aryl migration to provide the nitroarenes.
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