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.
Authors
- Maximilian Lübbesmeyer
- Philipp M. Holstein (ORCID: https://orcid.org/0000-0001-6952-7706)
- Mark Stradiotto (ORCID: https://orcid.org/0000-0002-6913-5160)
- Arthur E. Martell
- Mark J. Ford
- Sherif J. Kaldas (ORCID: https://orcid.org/0000-0003-2497-1963)
- Joshua W. M. MacMillan
- Giulio Volpin (ORCID: https://orcid.org/0000-0002-4348-9075)
- Nicolas Guimond (ORCID: https://orcid.org/0000-0001-5258-2557)
- Kathleen M. Morrison
Institutions
- Dalhousie University (CA)
- Bayer (Germany) (DE)
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