Direct Photochemical C–H Carboxylation of Aromatic Diamines with CO(2) under Electron-Donor- and Base-free Conditions

We report the photochemical carboxylation of o-phenylenedimamine in the absence of a base and an electron donor under an atmosphere of CO(2), which afforded 2,3-diaminobenzoic acid (DBA) in 28% synthetic yield and 0.22% quantum yield (Φ(%)). The synthetic yield of DBA in this reaction increased to 5...

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Autores principales: Matsumoto, Takeshi, Uchijo, Daiki, Koike, Takuji, Namiki, Ryoya, Chang, Ho-Chol
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2018
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6168591/
https://www.ncbi.nlm.nih.gov/pubmed/30279606
http://dx.doi.org/10.1038/s41598-018-33060-3
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author Matsumoto, Takeshi
Uchijo, Daiki
Koike, Takuji
Namiki, Ryoya
Chang, Ho-Chol
author_facet Matsumoto, Takeshi
Uchijo, Daiki
Koike, Takuji
Namiki, Ryoya
Chang, Ho-Chol
author_sort Matsumoto, Takeshi
collection PubMed
description We report the photochemical carboxylation of o-phenylenedimamine in the absence of a base and an electron donor under an atmosphere of CO(2), which afforded 2,3-diaminobenzoic acid (DBA) in 28% synthetic yield and 0.22% quantum yield (Φ(%)). The synthetic yield of DBA in this reaction increased to 58% (Φ(%) = 0.47) in the presence of Fe(II). The photochemical reaction described in this work provides an effective strategy to use light as the driving force for the direct carboxylation of organic molecules by CO(2).
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spelling pubmed-61685912018-10-05 Direct Photochemical C–H Carboxylation of Aromatic Diamines with CO(2) under Electron-Donor- and Base-free Conditions Matsumoto, Takeshi Uchijo, Daiki Koike, Takuji Namiki, Ryoya Chang, Ho-Chol Sci Rep Article We report the photochemical carboxylation of o-phenylenedimamine in the absence of a base and an electron donor under an atmosphere of CO(2), which afforded 2,3-diaminobenzoic acid (DBA) in 28% synthetic yield and 0.22% quantum yield (Φ(%)). The synthetic yield of DBA in this reaction increased to 58% (Φ(%) = 0.47) in the presence of Fe(II). The photochemical reaction described in this work provides an effective strategy to use light as the driving force for the direct carboxylation of organic molecules by CO(2). Nature Publishing Group UK 2018-10-02 /pmc/articles/PMC6168591/ /pubmed/30279606 http://dx.doi.org/10.1038/s41598-018-33060-3 Text en © The Author(s) 2018 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Matsumoto, Takeshi
Uchijo, Daiki
Koike, Takuji
Namiki, Ryoya
Chang, Ho-Chol
Direct Photochemical C–H Carboxylation of Aromatic Diamines with CO(2) under Electron-Donor- and Base-free Conditions
title Direct Photochemical C–H Carboxylation of Aromatic Diamines with CO(2) under Electron-Donor- and Base-free Conditions
title_full Direct Photochemical C–H Carboxylation of Aromatic Diamines with CO(2) under Electron-Donor- and Base-free Conditions
title_fullStr Direct Photochemical C–H Carboxylation of Aromatic Diamines with CO(2) under Electron-Donor- and Base-free Conditions
title_full_unstemmed Direct Photochemical C–H Carboxylation of Aromatic Diamines with CO(2) under Electron-Donor- and Base-free Conditions
title_short Direct Photochemical C–H Carboxylation of Aromatic Diamines with CO(2) under Electron-Donor- and Base-free Conditions
title_sort direct photochemical c–h carboxylation of aromatic diamines with co(2) under electron-donor- and base-free conditions
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6168591/
https://www.ncbi.nlm.nih.gov/pubmed/30279606
http://dx.doi.org/10.1038/s41598-018-33060-3
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