Mechanism of the Palladium-Catalyzed Intramolecular Hydroalkylation of 7-Octene-2,4-dione
- 30 January 2003
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (8) , 2056-2057
- https://doi.org/10.1021/ja0293002
Abstract
Cyclization of (E)-7,8-dideuterio-7-octene-2,4-dione [(E)-1-7,8-d(2)] catalyzed by PdCl(2)(CH(3)CN)(2) (2) formed cis-2-acyl-3,4-dideuteriocyclohexanone (cis-3-3,4-d(2)) in 64% yield as the exclusive isotopomer. This experiment, in conjunction with additional deuterium labeling experiments, was in accord with a mechanism for the conversion of 1 to 3 catalyzed by 2 involving attack of the enol carbon atom on a palladium-complexed olefin followed by palladium migration and protonolysis from a palladium enolate complex.Keywords
This publication has 19 references indexed in Scilit:
- Palladium-Catalyzed Intramolecular Oxidative Alkylation of Unactivated OlefinsJournal of the American Chemical Society, 2002
- Palladium-catalyzed cyclization of alkenyl β-keto esters in the presence of chlorotrimethylsilaneElectronic supplementary information (ESI) available: experimental procedures, analytical and spectroscopic data for new compounds and cyclohexanones. See http://www.rsc.org/suppdata/cc/b1/b111644d/Chemical Communications, 2002
- Mechanistic Studies of Pd(II)−α-Diimine-Catalyzed Olefin Polymerizations1Journal of the American Chemical Society, 2000
- 2,3-Dihalo-1-(phenylsulfonyl)-1-propenes as versatile reagents for the synthesis of annulated furans and cyclopentenonesThe Journal of Organic Chemistry, 1992
- Palladium(II)-catalyzed exchange and isomerization reactions. 14. Kinetics and stereochemistry of the isomerization and water exchange of 2-(methyl-d3)-4-methyl-1,1,1,5,5,5-hexafluoro-3-penten-2-ol in aqueous solution catalyzed by PdCl42-. Two new mechanistic probes for catalytic chemistryOrganometallics, 1991
- Cleavage of the rhenium-methyl bond of (.eta.-C5H5)Re(NO)(PPh3)(CH3) by protic and halogen electrophiles: stereochemistry at rheniumInorganic Chemistry, 1984
- Stereochemistry and mechanism for the palladium(II)-catalyzed oxidation of ethene in water (the Wacker process)Journal of the American Chemical Society, 1979
- Stereochemistry of the hydroxypalladation of ethylene. Evidence for trans addition in the wacker processJournal of the American Chemical Society, 1978
- The palladium(II) induced alkylation of styrenes. Kinetics, stereochemistry, and mechanismThe Journal of Organic Chemistry, 1977
- Stereochemistry of methoxypalladation of 2-butenesJournal of the American Chemical Society, 1973