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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...

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Autores principales: Dong, Chun-ping, Higashiura, Yuuki, Marui, Kuniaki, Kumazawa, Shun, Nomoto, Akihiro, Ueshima, Michio, Ogawa, Akiya
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
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.
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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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