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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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Detalles Bibliográficos
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:
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
Descripción
Sumario: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).