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

Quentin Lefebvre, Riccardo Porta, Anthony Millet, Jiaqi Jia, Magnus Rueping

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

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.
Original languageEnglish (US)
Pages (from-to)1363-1367
Number of pages5
JournalChemistry (Weinheim an der Bergstrasse, Germany)
Volume26
Issue number6
DOIs
StatePublished - Nov 28 2019

Bibliographical note

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).

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