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: | , , , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
November 24, 2025
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| 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 
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| Verfasserangaben: | K. Georg Leistikow, Alexander Wingelstern, Philipp Rohrmann, Jonas F. Wunsch, Jan Werst, Margit Brückner, Frank Rominger, Matthias Rudolph, and A. Stephen K. Hashmi |
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| 520 | |a 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. | ||
| 650 | 4 | |a C-H activation | |
| 650 | 4 | |a CAArCs | |
| 650 | 4 | |a Chelating carbene ligands | |
| 650 | 4 | |a Directing groups | |
| 650 | 4 | |a Palladium | |
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