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Microwave-assisted reduction of nitroarenes by aminothiophenol/dithiotreitol

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Abstract

Anilines are important intermediates in medicinal chemistry. They are usually obtained from the corresponding nitroarenes by reduction. The present work describes novel conditions for such transformation. Aminothiophenol reduced nitroarenes to corresponding anilines under mild and neutral conditions. The microwave assisted reduction proceeded well in MeOH for several functionalized nitroarenes. The reaction conditions were optimized such as the aminothiophenol could be used in a catalytic amount thanks to its regeneration by dithiotreitol. This methodology was applied to various nitroarenes including pnitrophenyl glycosides. A general mechanism is proposed.
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hal-01578547 , version 1 (29-08-2017)

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Cedric Peyrot, Thomas Vives, Laurent Legentil, Loïc Lemiègre, Richard Daniellou. Microwave-assisted reduction of nitroarenes by aminothiophenol/dithiotreitol. ChemistrySelect, 2017, 2 (18), pp.5214--5217. ⟨10.1002/slct.201700883⟩. ⟨hal-01578547⟩
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