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Facile access to chelating CAArC-phosphine (CAArCPhos) palladium complexes

In this article, we present a synthetic route to 4-(diphenyl-phosphino) isoindolium salts based on a new protecting group strategy. Key to success is the use of hemi-aminal methyl ether precursors, which serve as base-stable iminium salt equivalents that enable halogen-metal exchange and subsequent...

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Hauptverfasser: Leistikow, K. Georg (VerfasserIn) , Wingelstern, Alexander (VerfasserIn) , Rohrmann, Philipp (VerfasserIn) , Wunsch, Jonas (VerfasserIn) , Werst, Jan (VerfasserIn) , Brückner, Margit (VerfasserIn) , Rominger, Frank (VerfasserIn) , Rudolph, Matthias (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: November 24, 2025
In: Angewandte Chemie. International edition
Year: 2025, Jahrgang: 64, Heft: 48, Pages: 1-8
ISSN:1521-3773
DOI:10.1002/anie.202504316
Online-Zugang:Verlag, kostenfrei, Volltext: https://doi.org/10.1002/anie.202504316
Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.202504316
Volltext
Verfasserangaben:K. Georg Leistikow, Alexander Wingelstern, Philipp Rohrmann, Jonas F. Wunsch, Jan Werst, Margit Brückner, Frank Rominger, Matthias Rudolph, and A. Stephen K. Hashmi
Beschreibung
Zusammenfassung:In this article, we present a synthetic route to 4-(diphenyl-phosphino) isoindolium salts based on a new protecting group strategy. Key to success is the use of hemi-aminal methyl ether precursors, which serve as base-stable iminium salt equivalents that enable halogen-metal exchange and subsequent functionalization. After removal of the protecting group, the catalytically active palladium(II) complexes are formed of phosphine isoindolium salts by a CMD-like metalation process, producing the first examples of chelating cyclic amino(aryl) carbene complexes. Calculations on the mechanism support an acetate-assisted intramolecular palladation of the cyclic amino(aryl) carbene-phosphine (CAArCPhos) ligand enabled by the phosphine directing group through a six-membered transition state.
Beschreibung:Erstveröffentlichung: 15. Oktober 2025
Gesehen am 22.01.2025
Beschreibung:Online Resource
ISSN:1521-3773
DOI:10.1002/anie.202504316

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