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High Yield and Selective Electrocatalytic Reduction of Nitroarenes to Anilines using Redox Mediators

Stergiou, A. and Symes, M. (2022) High Yield and Selective Electrocatalytic Reduction of Nitroarenes to Anilines using Redox Mediators. [Data Collection] (Unpublished)

Datacite DOI: 10.5525/gla.researchdata.1279

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High yield and selective electrocatalytic reduction of nitroarenes to anilines using redox mediators
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Collection description

Anilines are major commodity chemicals used extensively in the production of pharmaceuticals, dyes and polymers. Typically, these anilines are produced from their corresponding nitrobenzene precursors by reaction with hydrogen at high temperatures. However, this route suffers from a number of drawbacks, including the requirement to handle hydrogen gas, rather harsh reaction conditions that lead to a lack of selectivity and/or toleration of certain functional groups, and questionable environmental sustainability. In light of this, routes to the reduction of nitrobenzenes to their aniline derivatives that operate at room temperature, in aqueous solvent and without the requirement to use harsh process conditions, hydrogen gas, or sacrificial reagents could be of tremendous benefit. Herein, we report on an electrocatalytic route to the reduction of nitrobenzenes to their aniline derivatives that works in aqueous solution at room temperature and pressure, where the electrons and protons required to reduce the nitrobenzenes are obtained from water. Excellent selectivity for the aniline derivatives is obtained for a range of nitrobenzenes, including for nitrobenzene substrates such as ortho-iodides that are very challenging to reduce effectively by other methods. Our approach relies on the use of a polyoxometalate redox mediator that shuts off the direct electro-reduction of the nitrobenzene at the electrode surface and thus prevents unproductive side reactions. Given the scale and current environmental impact of global aniline production, this electrochemical route holds promise for the development of more sustainable processes for the production of these vital chemical feedstocks.

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