Palladium‐Catalyzed Allylation of (Hetero)Aryl Fluorosulfates

Abstract Reported herein is the palladium‐catalyzed allylation of (hetero)aryl fluorosulfates. When employing a [Pd(cinnamyl)Cl] 2 /XantPhos catalyst system and using either allyl pinacolboronate or potassium allyltrifluoroborate, allyl (hetero)arene products were successfully prepared and isolated in synthetically useful yields, including examples featuring potentially reactive chloro groups. (Pseudo)halide chemoselectivity was further probed in intermolecular competition experiments, which revealed a preferred reactivity trend of Br > OFs >> Cl in the test system examined.

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Publication Details

Journal
ChemCatChem
Published
2025-03-28
DOI
https://doi.org/10.1002/cctc.202500526
Citations
1
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.79
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article

Palladium‐Catalyzed Allylation of (Hetero)Aryl Fluorosulfates

Maximilian Lübbesmeyer, Philipp M. Holstein, Mark Stradiotto, Arthur E. Martell et al.
1 citations
ChemCatChem
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0.79
article

Palladium‐Catalyzed Allylation of (Hetero)Aryl Fluorosulfates

Maximilian Lübbesmeyer, Philipp M. Holstein, Mark Stradiotto, Arthur E. Martell, Mark J. Ford, Sherif J. Kaldas, Joshua W. M. MacMillan, Giulio Volpin, Nicolas Guimond, Kathleen M. Morrison
article en
1 citations

Abstract

Abstract Reported herein is the palladium‐catalyzed allylation of (hetero)aryl fluorosulfates. When employing a [Pd(cinnamyl)Cl] 2 /XantPhos catalyst system and using either allyl pinacolboronate or potassium allyltrifluoroborate, allyl (hetero)arene products were successfully prepared and isolated in synthetically useful yields, including examples featuring potentially reactive chloro groups. (Pseudo)halide chemoselectivity was further probed in intermolecular competition experiments, which revealed a preferred reactivity trend of Br > OFs >> Cl in the test system examined.

ChemCatChemVol. 17(11)
Dalhousie University (CA), Bayer (Germany) (DE)
Openalex Percentile: Top 29%
Fluorine in Organic Chemistry
0.79
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