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Metal-Free Oxidative Coupling of Benzylamines to Imines under an Oxygen Atmosphere Promoted Using Salicylic Acid Derivatives as Organocatalysts
[Image: see text] The oxidative coupling of benzylamines proceeds efficiently using salicylic acid derivatives as organocatalysts under an oxygen atmosphere, affording the corresponding N-benzylidenebenzylamines in high yields. Electron-rich salicylic acid derivatives such as 4,6-dimethoxysalicylic...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2016
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6640803/ https://www.ncbi.nlm.nih.gov/pubmed/31457163 http://dx.doi.org/10.1021/acsomega.6b00235 |
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author | Dong, Chun-ping Higashiura, Yuuki Marui, Kuniaki Kumazawa, Shun Nomoto, Akihiro Ueshima, Michio Ogawa, Akiya |
author_facet | Dong, Chun-ping Higashiura, Yuuki Marui, Kuniaki Kumazawa, Shun Nomoto, Akihiro Ueshima, Michio Ogawa, Akiya |
author_sort | Dong, Chun-ping |
collection | PubMed |
description | [Image: see text] The oxidative coupling of benzylamines proceeds efficiently using salicylic acid derivatives as organocatalysts under an oxygen atmosphere, affording the corresponding N-benzylidenebenzylamines in high yields. Electron-rich salicylic acid derivatives such as 4,6-dimethoxysalicylic acid and 4,6-dihydroxysalicylic acid exhibit excellent catalytic activities for the oxidative coupling of benzylamines to give the corresponding imines. This amine oxidation can also be applied to the synthesis of nitrogen-containing heterocycles such as benzimidazole derivatives. Furthermore, to recycle the catalyst, silica gel supported with 4.7 wt % of 4,6-dihydroxysalicylic acid is prepared, which acts as a recyclable catalyst, oxidizing benzylamine to imine four times successfully. |
format | Online Article Text |
id | pubmed-6640803 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-66408032019-08-27 Metal-Free Oxidative Coupling of Benzylamines to Imines under an Oxygen Atmosphere Promoted Using Salicylic Acid Derivatives as Organocatalysts Dong, Chun-ping Higashiura, Yuuki Marui, Kuniaki Kumazawa, Shun Nomoto, Akihiro Ueshima, Michio Ogawa, Akiya ACS Omega [Image: see text] The oxidative coupling of benzylamines proceeds efficiently using salicylic acid derivatives as organocatalysts under an oxygen atmosphere, affording the corresponding N-benzylidenebenzylamines in high yields. Electron-rich salicylic acid derivatives such as 4,6-dimethoxysalicylic acid and 4,6-dihydroxysalicylic acid exhibit excellent catalytic activities for the oxidative coupling of benzylamines to give the corresponding imines. This amine oxidation can also be applied to the synthesis of nitrogen-containing heterocycles such as benzimidazole derivatives. Furthermore, to recycle the catalyst, silica gel supported with 4.7 wt % of 4,6-dihydroxysalicylic acid is prepared, which acts as a recyclable catalyst, oxidizing benzylamine to imine four times successfully. American Chemical Society 2016-11-04 /pmc/articles/PMC6640803/ /pubmed/31457163 http://dx.doi.org/10.1021/acsomega.6b00235 Text en Copyright © 2016 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 | Dong, Chun-ping Higashiura, Yuuki Marui, Kuniaki Kumazawa, Shun Nomoto, Akihiro Ueshima, Michio Ogawa, Akiya Metal-Free Oxidative Coupling of Benzylamines to Imines under an Oxygen Atmosphere Promoted Using Salicylic Acid Derivatives as Organocatalysts |
title | Metal-Free Oxidative Coupling of Benzylamines to Imines
under an Oxygen Atmosphere Promoted Using Salicylic Acid Derivatives
as Organocatalysts |
title_full | Metal-Free Oxidative Coupling of Benzylamines to Imines
under an Oxygen Atmosphere Promoted Using Salicylic Acid Derivatives
as Organocatalysts |
title_fullStr | Metal-Free Oxidative Coupling of Benzylamines to Imines
under an Oxygen Atmosphere Promoted Using Salicylic Acid Derivatives
as Organocatalysts |
title_full_unstemmed | Metal-Free Oxidative Coupling of Benzylamines to Imines
under an Oxygen Atmosphere Promoted Using Salicylic Acid Derivatives
as Organocatalysts |
title_short | Metal-Free Oxidative Coupling of Benzylamines to Imines
under an Oxygen Atmosphere Promoted Using Salicylic Acid Derivatives
as Organocatalysts |
title_sort | metal-free oxidative coupling of benzylamines to imines
under an oxygen atmosphere promoted using salicylic acid derivatives
as organocatalysts |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6640803/ https://www.ncbi.nlm.nih.gov/pubmed/31457163 http://dx.doi.org/10.1021/acsomega.6b00235 |
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