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Surfactant-Assisted Selective Oxidation of Aromatic Amines to Nitro Compounds by in Situ-Formed Performic Acid

[Image: see text] Development of novel and greener methods for the selective oxidation of various organic compounds is a challenging task. Herein, a novel protocol for the selective oxidation of aromatic amines to nitroaromatics at room temperature is developed. The oxidation reaction was carried ou...

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Autores principales: Ravi, Krishnan, Bankar, Balasaheb D., Jindani, Sana, Biradar, Ankush V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648202/
https://www.ncbi.nlm.nih.gov/pubmed/31460036
http://dx.doi.org/10.1021/acsomega.9b00543
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author Ravi, Krishnan
Bankar, Balasaheb D.
Jindani, Sana
Biradar, Ankush V.
author_facet Ravi, Krishnan
Bankar, Balasaheb D.
Jindani, Sana
Biradar, Ankush V.
author_sort Ravi, Krishnan
collection PubMed
description [Image: see text] Development of novel and greener methods for the selective oxidation of various organic compounds is a challenging task. Herein, a novel protocol for the selective oxidation of aromatic amines to nitroaromatics at room temperature is developed. The oxidation reaction was carried out using a mixture of formic acid and aqueous hydrogen peroxide, which resulted in the in situ formation of performic acid. Further, improvement of selectivity was studied using different surfactants, of which cetyltrimethylammonium bromide (CTAB) gave the highest selectivity (85%) toward nitrobenzene. The role of CTAB in achieving higher selectivity is discussed. Under optimized reaction conditions, various substituted amines were successfully oxidized to corresponding nitro compounds. It is worth mentioning that this is the first report on oxidation of amines to nitro compounds in an aqueous medium with high selectivity.
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spelling pubmed-66482022019-08-27 Surfactant-Assisted Selective Oxidation of Aromatic Amines to Nitro Compounds by in Situ-Formed Performic Acid Ravi, Krishnan Bankar, Balasaheb D. Jindani, Sana Biradar, Ankush V. ACS Omega [Image: see text] Development of novel and greener methods for the selective oxidation of various organic compounds is a challenging task. Herein, a novel protocol for the selective oxidation of aromatic amines to nitroaromatics at room temperature is developed. The oxidation reaction was carried out using a mixture of formic acid and aqueous hydrogen peroxide, which resulted in the in situ formation of performic acid. Further, improvement of selectivity was studied using different surfactants, of which cetyltrimethylammonium bromide (CTAB) gave the highest selectivity (85%) toward nitrobenzene. The role of CTAB in achieving higher selectivity is discussed. Under optimized reaction conditions, various substituted amines were successfully oxidized to corresponding nitro compounds. It is worth mentioning that this is the first report on oxidation of amines to nitro compounds in an aqueous medium with high selectivity. American Chemical Society 2019-05-30 /pmc/articles/PMC6648202/ /pubmed/31460036 http://dx.doi.org/10.1021/acsomega.9b00543 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Ravi, Krishnan
Bankar, Balasaheb D.
Jindani, Sana
Biradar, Ankush V.
Surfactant-Assisted Selective Oxidation of Aromatic Amines to Nitro Compounds by in Situ-Formed Performic Acid
title Surfactant-Assisted Selective Oxidation of Aromatic Amines to Nitro Compounds by in Situ-Formed Performic Acid
title_full Surfactant-Assisted Selective Oxidation of Aromatic Amines to Nitro Compounds by in Situ-Formed Performic Acid
title_fullStr Surfactant-Assisted Selective Oxidation of Aromatic Amines to Nitro Compounds by in Situ-Formed Performic Acid
title_full_unstemmed Surfactant-Assisted Selective Oxidation of Aromatic Amines to Nitro Compounds by in Situ-Formed Performic Acid
title_short Surfactant-Assisted Selective Oxidation of Aromatic Amines to Nitro Compounds by in Situ-Formed Performic Acid
title_sort surfactant-assisted selective oxidation of aromatic amines to nitro compounds by in situ-formed performic acid
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648202/
https://www.ncbi.nlm.nih.gov/pubmed/31460036
http://dx.doi.org/10.1021/acsomega.9b00543
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