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

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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.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: One Amine–3 Tasks: Reductive Coupling of Imines with Olefins in Batch and Flow ; volume:26 ; number:6 ; year:2020 ; pages:1363-1367 ; extent:5
Chemistry - a European journal ; 26, Heft 6 (2020), 1363-1367 (gesamt 5)

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

DOI: 10.1002/chem.201904483

URN: urn:nbn:de:101:1-2022060307374143163388

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:35 AM CEST

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Associated

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

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Titanium-mediated reductive cross-coupling reactions of imines with terminal alkynes: An efficient route for the synthesis of stereodefined allylic amines

Solvent design for catalyst recycling of rhodium/amine catalysts via scCO2 extraction in the reductive hydroformylation of alpha olefins

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Copper amine oxidases catalyze the oxidative deamination and hydrolysis of cyclic imines

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

Efficient synthesis of amines : from reductive amination of aldehydes to hydroaminomethylation of olefins

Hochschulschrift

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Reductive Carboamination of Olefins with Aryldiazonium Salts

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Electrophotocatalytic hydrogenation of imines and reductive functionalization of aryl halides

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Functionalized α‐Fluorinated Amines from Imines and Enol Ethers

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Titanium-mediated reductive cross-coupling reactions of imines with terminal alkynes: An efficient route for the synthesis of stereodefined allylic amines

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Solvent design for catalyst recycling of rhodium/amine catalysts via scCO2 extraction in the reductive hydroformylation of alpha olefins

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Palladium‐Catalyzed Hydroaminocarbonylation of Olefins with Aliphatic Amines without Additives

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Copper amine oxidases catalyze the oxidative deamination and hydrolysis of cyclic imines

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A Selective and General Cobalt‐Catalyzed Hydroaminomethylation of Olefins to Amines

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