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

Satenik Mkrtchyan, Vishal B. Purohit, Sehrish Sarfaraz, Muhammad Yar, Khurshid Ayub, Viktor O. Iaroshenko

2023ACS Sustainable Chemistry & Engineering22 citationsDOIOpen Access PDF

Abstract

High Resolution Image Download MS PowerPoint Slide A metal-free strategy for the supramolecular reduction of nitroarenes in a cucurbit[7]uril (CB[7]) cavity has been developed under blue light (390 nm) irradiation using a mixture of aqueous sodium chloride/dichloromethane as 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 supramolecular reduction of nitroarenes into a CB[7] cavity. The mechanism of this transformation was simulated by the DFT method.

Topics & Concepts

Supramolecular chemistryDichloromethaneAqueous solutionChemistryNitroAqueous mediumMetalCombinatorial chemistryOrganic chemistryMoleculeSolventAlkylSupramolecular Chemistry and ComplexesNanomaterials for catalytic reactionsCovalent Organic Framework Applications