Abstract
Aim and Objective: A simple catalytic method has been developed to achieve the reduction of nitroarenes with NaBH4 using diphenyl diselenide catalyst in order to obtain the azoxyarene, azoarene products under mild conditions.
Materials and Methods: The reduction of different substituted nitroarenes was realized in alkaline ethanolic solution using mild sodium borohydride in the presence of diphenyl diselenide as an electron-transfer catalyst. The reactions were performed sometimes at room temperature and sometimes at refluxing conditions.
Results: Diphenyl diselenide which is reduced to sodium phenylselenolate, presenting an electron transfer agent successfully permitted to reduce several nitroarenes, bearing different substituent groups whose electronic effects promote the formation of the azoxy or azo compounds.
Conclusion: Treatment of nitroarenes with sodium borohydride in alkaline ethanol in the presence of catalytic amounts of diphenyl diselenide at room temperature leads to obtain the corresponding azoxy compounds in good yields by reaction with sodium phenylselenolate generated in situ. At higher temperature, further reduction to azo compounds occurs. Therefore, the results have indicated that the electronic effects of substituent groups rigorously take part in determination of their reduction efficiencies.
Keywords: Nitroarenes, diphenyl diselenide, phenylselenolate, azoxyarene, azoarene, sodium borohydride.
Current Organic Synthesis
Title:Diphenyl Diselenide – catalyzed Reductive Coupling of Nitroarenes to Aromatic Azo and Azoxy Compounds with Sodium Borohydride in Alkaline Ethanol
Volume: 15 Issue: 8
Author(s): Nadjah Belattar*, Samir Benayache and Fadila Benayache
Affiliation:
- Research Unity of Valorization of Natural Resources- Bioactive Molecules, Physicochemical and Biological Analyses, Department of Chemistry, Faculty of Exact Sciences, University of Mentouri- Brothers, Constantine-1, 25000,Algeria
Keywords: Nitroarenes, diphenyl diselenide, phenylselenolate, azoxyarene, azoarene, sodium borohydride.
Abstract: Aim and Objective: A simple catalytic method has been developed to achieve the reduction of nitroarenes with NaBH4 using diphenyl diselenide catalyst in order to obtain the azoxyarene, azoarene products under mild conditions.
Materials and Methods: The reduction of different substituted nitroarenes was realized in alkaline ethanolic solution using mild sodium borohydride in the presence of diphenyl diselenide as an electron-transfer catalyst. The reactions were performed sometimes at room temperature and sometimes at refluxing conditions.
Results: Diphenyl diselenide which is reduced to sodium phenylselenolate, presenting an electron transfer agent successfully permitted to reduce several nitroarenes, bearing different substituent groups whose electronic effects promote the formation of the azoxy or azo compounds.
Conclusion: Treatment of nitroarenes with sodium borohydride in alkaline ethanol in the presence of catalytic amounts of diphenyl diselenide at room temperature leads to obtain the corresponding azoxy compounds in good yields by reaction with sodium phenylselenolate generated in situ. At higher temperature, further reduction to azo compounds occurs. Therefore, the results have indicated that the electronic effects of substituent groups rigorously take part in determination of their reduction efficiencies.
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Cite this article as:
Belattar Nadjah*, Benayache Samir and Benayache Fadila , Diphenyl Diselenide – catalyzed Reductive Coupling of Nitroarenes to Aromatic Azo and Azoxy Compounds with Sodium Borohydride in Alkaline Ethanol, Current Organic Synthesis 2018; 15 (8) . https://dx.doi.org/10.2174/1570179415666181025151130
DOI https://dx.doi.org/10.2174/1570179415666181025151130 |
Print ISSN 1570-1794 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6271 |
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