Photoreduction of Nitro (Hetero)arenes to (Hetero)arylhydroxylamines by <i>iso</i>Propanol in Flow: Application to the Synthesis of Paracetamol

The photoreduction of substituted nitro (hetero)arenes by <i>i</i>PrOH has been achieved in batch and continuous flow chemistry. Good yields of <i>N</i>-(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 <i>N</i>-phenylhydroxylamine followed by an original 1,5-rearrangement.