Metal-Free Supramolecular Reduction of Nitro Compounds into the Cucurbit[7]uril Cavity: Testing the Enabling Technique in Aqueous Media

This protocol describes metal-free supramolecular reductionof nitroarenes into the cucurbit[7]-uril cavity under the blue lightirradiation (390 nm). A metal-free strategy for the supramolecular reductionof nitroarenesin a cucurbit[7]-uril (CB[7]) cavity has been developed under bluelight (390 nm) irradiation using a mixture of aqueous sodium chloride/dichloromethaneas the reaction media. The protocol was found to be simple, efficient,and environmentally benign to obtain diversely substituted anilines,including heterocyclic and aliphatic amines with excellent yields.This is the first ever report describing the blue light-driven supramolecularreduction of nitroarenes into a CB[7] cavity. The mechanism of thistransformation was simulated by the DFT method.

Automated summary

This protocol presents a metal-free supramolecular reduction method utilizing blue light (390 nm) to drive the reduction of nitroarenes into a cucurbit[7]-uril (CB[7]) cavity. The reaction was conducted using a mixture of aqueous sodium chloride and dichloromethane as the reaction media, resulting in the formation of various substituted anilines with high yields. The mechanism of this transformation was simulated using the DFT method.