Unusual Allylpalladium Carboxylate Complexes: Identification of the Resting State of Catalytic Enantioselective Decarboxylative Allylic Alkylation Reactions of Ketones

Unusual Allylpalladium Carboxylate Complexes: Identification of the Resting State of Catalytic Enantioselective Decarboxylative Allylic Alkylation Reactions of Ketones

Palladium pop rocks: Hold on to your CO2! Enantioselective palladium‐catalyzed decarboxylative alkylation of ketone enolates proceeds via η1‐σ‐allyl palladium–carboxylate complexes, such as 1 (Pd yellow, O red, N blue, P purple), by slow loss of CO2. Reminiscent of pop rock candy, impure samples of...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2009-09, Vol.48 (37), p.6840-6843
Hauptverfasser: Sherden, Nathaniel H, Behenna, Douglas C, Virgil, Scott C, Stoltz, Brian M
Format: Artikel
Sprache:eng
Schlagworte:
Alkylation
allylic alkylation
asymmetric catalysis
carboxylate ligands
Carboxylic Acids - chemistry
Catalysis
Crystallography, X-Ray
Ketones - chemistry
Molecular Conformation
palladium
Palladium - chemistry
reaction mechanisms
Stereoisomerism
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Zusammenfassung:Palladium pop rocks: Hold on to your CO2! Enantioselective palladium‐catalyzed decarboxylative alkylation of ketone enolates proceeds via η1‐σ‐allyl palladium–carboxylate complexes, such as 1 (Pd yellow, O red, N blue, P purple), by slow loss of CO2. Reminiscent of pop rock candy, impure samples of 1 expel a gas (presumably CO2) in the solid state and effervesce in solution.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200902575