Palladium-Catalyzed Monoarylation of Cyclopropylamine

A novel palladium-catalyzed protocol for the monoarylation of cyclopropylamine using the sterically demanding and electron-rich adamantyl-substituted ylide-functionalized phosphine (YPhos) adYPhos is reported. This method enables the efficient coupling of a wide range of (hetero)aryl chlorides at room temperature. The reported ligand enhances the scope for the application of YPhos ligands in amination reactions on more challenging substrates. The protocol is versatile, accommodating various functional groups and extending to larger cycloalkylamines, all accessible under feasible and mild conditions.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-08-20
DOI
https://doi.org/10.1021/acs.joc.5c01233
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Palladium-Catalyzed Monoarylation of Cyclopropylamine

Jens Handelmann, Viktoria H. Gessner, Nicolas Kaiser, Lea Räkow
The Journal of Organic Chemistry
Catalytic Cross-Coupling Reactions
article

Palladium-Catalyzed Monoarylation of Cyclopropylamine

Jens Handelmann, Viktoria H. Gessner, Nicolas Kaiser, Lea Räkow
article en

Abstract

A novel palladium-catalyzed protocol for the monoarylation of cyclopropylamine using the sterically demanding and electron-rich adamantyl-substituted ylide-functionalized phosphine (YPhos) adYPhos is reported. This method enables the efficient coupling of a wide range of (hetero)aryl chlorides at room temperature. The reported ligand enhances the scope for the application of YPhos ligands in amination reactions on more challenging substrates. The protocol is versatile, accommodating various functional groups and extending to larger cycloalkylamines, all accessible under feasible and mild conditions.

The Journal of Organic ChemistryVol. 90(34)
Ruhr University Bochum (DE)
Fonds der Chemischen Industrie, European Commission, Deutsche Forschungsgemeinschaft, HORIZON EUROPE European Research Council
Openalex Percentile: Top 84%
Catalytic Cross-Coupling Reactions
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Palladium-Catalyzed Monoarylation of Cyclopropylamine — Jens Handelmann, Viktoria H. Gessner, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS