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Iodine(III)-Catalyzed Electrophilic Nitration of Phenols via Non-Brønsted Acidic NO 2 + Generation.
Organic Letters 2019 Februrary 13
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-Brønsted 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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