Journal
ORGANIC LETTERS
Volume 21, Issue 5, Pages 1315-1319Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b04141
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Funding
- CONACyT [CB-2013/220836]
- JSPS KAKENHI [JP26220803, JP17H06450]
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The first catalytic procedure for the electrophilic nitration of phenols was developed using iodosylbenzene as an organocatalyst based on iodine(III) and aluminum nitrate as a nitro group source. This atom-economic protocol occurs under mild, non-Bronsted acidic and open-flask reaction conditions with a broad functional-group tolerance including several heterocycles. Density functional theory (DFT) calculations at the (SMD:MeCN)Mo8-HX/(LANLo8+f,6-311+G*) level indicated that the reaction proceeds through a cationic pathway that efficiently generates the NO2+ ion, which is the nitrating species under neutral conditions.
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