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

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

doi:10.1002/chem.201904483

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 journal › Article › peer-review

12 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 language	English (US)
Pages (from-to)	1363-1367
Number of pages	5
Journal	Chemistry (Weinheim an der Bergstrasse, Germany)
Volume	26
Issue number	6
DOIs	https://doi.org/10.1002/chem.201904483
State	Published - 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).

Access to Document

10.1002/chem.201904483

https://repository.kaust.edu.sa/bitstream/10754/661469/1/chem.201904483.pdf

Cite this

@article{d6625bda3e7b473d83b2d4efee13b947,

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

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.",

author = "Quentin Lefebvre and Riccardo Porta and Anthony Millet and Jiaqi Jia and Magnus Rueping",

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).",

year = "2019",

month = nov,

day = "28",

doi = "10.1002/chem.201904483",

language = "English (US)",

volume = "26",

pages = "1363--1367",

journal = "Chemistry (Weinheim an der Bergstrasse, Germany)",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "6",

}

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 -

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

Abstract

Bibliographical note

Access to Document

Other files and links

Fingerprint

Cite this