TY - JOUR
T1 - One Amine-3 Tasks: Reductive Coupling of Imines with Olefins in Batch and Flow
AU - Lefebvre, Quentin
AU - Porta, Riccardo
AU - Millet, Anthony
AU - Jia, Jiaqi
AU - Rueping, Magnus
N1 - KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: R.P. thanks DAAD for a scholarship. The research leading to these results has received funding from the European Research Council under the European Union's Seventh Framework Programme (FP/2007-2013)/ERC Grant Agreement no. 617044 (SunCatChem).
PY - 2019/11/28
Y1 - 2019/11/28
N2 - 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.
AB - 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.
UR - http://hdl.handle.net/10754/661469
UR - https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201904483
UR - http://www.scopus.com/inward/record.url?scp=85078691872&partnerID=8YFLogxK
U2 - 10.1002/chem.201904483
DO - 10.1002/chem.201904483
M3 - Article
C2 - 31777987
SN - 0947-6539
VL - 26
SP - 1363
EP - 1367
JO - Chemistry (Weinheim an der Bergstrasse, Germany)
JF - Chemistry (Weinheim an der Bergstrasse, Germany)
IS - 6
ER -