Palladium-Catalyzed Intramolecular Hydroalkylation of Alkenyl- ?-Keto Esters, ?-Aryl Ketones, and Alkyl Ketones in the Presence of Me3SiCl or HCl

2004 ◽  
Vol 10 (24) ◽  
pp. 6333-6342 ◽  
Author(s):  
Xiaoqing Han ◽  
Xiang Wang ◽  
Tao Pei ◽  
Ross A. Widenhoefer
Keyword(s):  
Keto Esters ◽  
Aryl Ketones ◽  
Palladium Catalyzed

scholarly journals Palladium-catalyzed alkylation of unactivated olefins

2004 ◽  
Vol 76 (3) ◽  
pp. 671-678 ◽  
Author(s):  
Ross A. Widenhoefer
Keyword(s):  
Good Yield ◽  
Catalytic Amount ◽  
Outer Sphere ◽  
Deuterium Labeling ◽  
Carbon Nucleophiles ◽  
Keto Esters ◽  
Reactive Carbon ◽  
Aryl Ketones ◽  
Palladium Catalyzed ◽  
Hydride Elimination

The reaction of a 3-butenyl β-diketone with a catalytic amount of PdCl2(CH3CN)2 in dioxane at room temperature led to olefin hydroalkylation and formation of the corresponding 2-acylcyclohexanone in good yield as a single regioisomer. Deuterium-labeling experiments for the hydroalkylation of 7-octene-2,4-dione were in accord with a mechanism involving outer-sphere attack of the pendant enol on a palladium-complexed olefin to form a palladium cyclohexyl species, followed by palladium migration via iterative β-hydride elimination/addition and protonolysis from a palladium enolate complex. In comparison to a 3-butenyl β-diketone, reaction of a 4-pentenyl β-diketone with a catalytic amount of PdCl2(CH3CN)2 in the presence of CuCl2 led to oxidative alkylation and formation of the corresponding 2-acyl-3-methyl-2-cyclohexenone in good yield as a single isomer. Unactivated olefins tethered to less reactive carbon nucleophiles such as β-keto esters, α-aryl ketones, and even dialkyl ketones underwent palladium-catalyzed hydroalkylation in the presence of Me3SiCl or HCl to form the corresponding cyclohexanones in moderate-to-good yield with high regioselectivity.

One-pot efficient synthesis of aryl α-keto esters from aryl-ketones

Tetrahedron ◽  
2009 ◽  
Vol 65 (47) ◽  
pp. 9797-9800 ◽  
Author(s):  
Jing Zhuang ◽  
Changqing Wang ◽  
Fang Xie ◽  
Wanbin Zhang
Keyword(s):  
Efficient Synthesis ◽  
One Pot ◽  
Keto Esters ◽  
Aryl Ketones

Palladium Catalyzed Heck Reaction of Arenediazonium Tetrafluoroborate Salts with Baylis—Hillman Adducts: Production of α-Benzyl-β-keto Esters.

ChemInform ◽  
2006 ◽  
Vol 37 (22) ◽  
Author(s):  
Rolando Perez ◽  
Demetrius Veronese ◽  
Fernando Coelho ◽  
O. A. C. Antunes
Keyword(s):  
Heck Reaction ◽  
Keto Esters ◽  
Palladium Catalyzed

Efficient synthesis of alkyl aryl ketones & ketals via palladium-catalyzed regioselective arylation of vinyl ethers

2010 ◽  
Vol 8 (9) ◽  
pp. 2012 ◽  
Author(s):  
Mingcui Liu ◽  
Zeynab Hyder ◽  
Yawei Sun ◽  
Weijun Tang ◽  
Lijin Xu ◽  
...  
Keyword(s):  
Efficient Synthesis ◽  
Vinyl Ethers ◽  
Alkyl Aryl ◽  
Aryl Ketones ◽  
Palladium Catalyzed
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