Chiral Monodentate Phosphines and Bulky Carboxylic Acids: Cooperative Effects in Palladium-Catalyzed Enantioselective C(sp3)-H Functionalization

Chiral Monodentate Phosphines and Bulky Carboxylic Acids: Cooperative Effects in Palladium-Catalyzed Enantioselective C(sp3)-H Functionalization

Teaming up: The important indoline scaffold is provided with enantiomeric ratios of up to 98:2 in palladium(0)‐catalyzed C(sp3)–H activations of aryl triflates. The key is the combination of the electron‐rich monodentate Sagephos and the bulky 9H‐xanthene‐9‐carboxylic acid. Both participate in a hig...

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Veröffentlicht in:Angewandte Chemie International Edition 2012-02, Vol.51 (9), p.2238-2242
Hauptverfasser: Saget, Tanguy, Lemouzy, Sébastien J., Cramer, Nicolai
Format: Artikel
Sprache:eng
Schlagworte:
Activation
Aromatic compounds
asymmetric catalysis
Carboxylic acids
cooperative effects
CH activation
palladium
Phosphines
Scaffolds
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Zusammenfassung:Teaming up: The important indoline scaffold is provided with enantiomeric ratios of up to 98:2 in palladium(0)‐catalyzed C(sp3)–H activations of aryl triflates. The key is the combination of the electron‐rich monodentate Sagephos and the bulky 9H‐xanthene‐9‐carboxylic acid. Both participate in a highly cooperative manner in the enantiodetermining concerted‐deprotonation‐metalation step (see scheme, Tf=triflate).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201108511