Synthesis of Allenyl Ketones by the Palladium-Catalyzed Carbonylation of 2-Alkynyl Carbonates in the Presence of Soft Carbon Nucleophiles

Synlett ◽  
1991 ◽  
Vol 1991 (10) ◽  
pp. 697-698 ◽  
Author(s):  
Tadakatsu Mandai ◽  
Hiroaki Kunitomi ◽  
Kiyoto Higashi ◽  
Mikio Kawada ◽  
Jiro Tsuji
Keyword(s):  
Carbon Nucleophiles ◽  
Palladium Catalyzed ◽  
Soft Carbon

Synthesis of Allenyl Ketones by the Palladium-Catalyzed Carbonylation of 2-Alkynyl Carbonates in the Presence of Soft Carbon Nucleophiles

Synlett ◽  
1991 ◽  
Vol 1991 (09) ◽  
pp. 697-698 ◽  
Author(s):  
Tadakatsu Mandai ◽  
Hiroaki Kunitomi ◽  
Kiyoto Higashi ◽  
Mikio Kawada ◽  
Jiro Tsuji
Keyword(s):  
Carbon Nucleophiles ◽  
Palladium Catalyzed ◽  
Soft Carbon

Palladium-Catalyzed Reactions of Soft Carbon Nucleophiles with Dienes, Vinylcyclopropanes, and Related Compounds

ChemInform ◽  
2003 ◽  
Vol 34 (25) ◽  
Author(s):  
Hiroyuki Nakamura ◽  
Yoshinori Yamamoto
Keyword(s):  
Carbon Nucleophiles ◽  
Palladium Catalyzed ◽  
Soft Carbon ◽  
Catalyzed Reactions ◽  
Related Compounds

ChemInform Abstract: Synthesis of Allenyl Ketones by the Palladium-Catalyzed Carbonylation of 2-Alkynyl Carbonates in the Presence of Soft Carbon Nucleophiles.

ChemInform ◽  
2010 ◽  
Vol 23 (17) ◽  
pp. no-no
Author(s):  
T. MANDAI ◽  
H. KUNITOMI ◽  
K. HIGASHI ◽  
M. KAWADA ◽  
J. TSUJI
Keyword(s):  
Carbon Nucleophiles ◽  
Palladium Catalyzed ◽  
Soft Carbon

ChemInform Abstract: Allylsilanes as Carbon Nucleophiles in the Palladium-Catalyzed 1,4- Oxidation of Conjugated Dienes.

ChemInform ◽  
2010 ◽  
Vol 28 (23) ◽  
pp. no-no
Author(s):  
A. M. CASTANO ◽  
B. A. PERSSON ◽  
J.-E. BAECKVALL
Keyword(s):  
Conjugated Dienes ◽  
Carbon Nucleophiles ◽  
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.

ChemInform Abstract: Palladium-Catalyzed Carbene Insertion and Trapping with Carbon Nucleophiles.

ChemInform ◽  
2008 ◽  
Vol 39 (41) ◽  
Author(s):  
Sean K. J. Devine ◽  
David L. Van Vranken
Keyword(s):  
Carbon Nucleophiles ◽  
Carbene Insertion ◽  
Palladium Catalyzed

Allenes as Carbon Nucleophiles in Palladium-Catalyzed Reactions:  Observation of Anti Attack of Allenes on (π-Allyl)palladium Complexes

2002 ◽  
Vol 124 (38) ◽  
pp. 11246-11247 ◽  
Author(s):  
Johan Franzén ◽  
Joakim Löfstedt ◽  
Ismet Dorange ◽  
Jan-E. Bäckvall
Keyword(s):  
Palladium Complexes ◽  
Carbon Nucleophiles ◽  
Palladium Catalyzed ◽  
Catalyzed Reactions
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