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One Amine–3 Tasks: Reductive Coupling of Imines with Olefins in Batch and Flow

Owing to their wide range of biological properties, γ‐aminobutyric acid derivatives (GABA) have been extensively studied and found noteworthy industrial applications. However, atom‐economical and efficient processes for their production are scarce and would greatly benefit from further investigation...

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Detalles Bibliográficos
Autores principales: Lefebvre, Quentin, Porta, Riccardo, Millet, Anthony, Jia, Jiaqi, Rueping, Magnus
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7027816/
https://www.ncbi.nlm.nih.gov/pubmed/31777987
http://dx.doi.org/10.1002/chem.201904483
Descripción
Sumario:Owing to their wide range of biological properties, γ‐aminobutyric acid derivatives (GABA) have been extensively studied and found noteworthy industrial applications. However, atom‐economical and efficient processes for their production are scarce and would greatly benefit from further investigations. Herein, we demonstrate that an iridium‐based photocatalyst promotes the direct reductive cross‐coupling of imines with olefins upon irradiation with visible light to give GABA derivatives in good yields and selectivities. We also stress the enabling triple role of tributylamine additive in this process, discuss the advantages of strategies based on proton‐coupled electron transfer (PCET) and demonstrate the scale‐up of this reaction in continuous flow.