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Flow chemistry demonstrates efficient photoreduction of nitroarenes to hydroxylamines, suggesting streamlined paracetamol synthesis.
The photoreduction of substituted nitro (hetero)arenes by iPrOH has been achieved in batch and continuous flow chemistry. Good yields of N-(hetero)arylhydroxylamines were obtained when nitrobenzene was substituted by electron-withdrawing groups. The reaction is chemoselective as nitriles, esters, carboxylic acids, ketones, and halides are not reduced. The application of the photoreduction of nitrobenzene to the synthesis of paracetamol was achieved by the acetylation of N-phenylhydroxylamine followed by an original 1,5-rearrangement.
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Nabokoff et al. (2025) studied this question.
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