Catalyzed catalysis using carbophilic Lewis acidic gold and Lewis basic palladium: synthesis of substituted butenolides and isocoumarins.

Autor: Shi Y; Department of Chemistry, University of California, Irvine, California 92697-2025, USA., Roth KE, Ramgren SD, Blum SA
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2009 Dec 23; Vol. 131 (50), pp. 18022-3.
DOI: 10.1021/ja9068497
Abstrakt: A new strategy for gold and palladium dual-catalytic reactivity and turnover, called catalyzed catalysis, enhanced the synthetic usefulness of vinylgold intermediates by providing dual-catalytic carbon-carbon cross-coupling as an alternative to protodemetalation. This protocol enabled the synthesis of substituted butenolides and isocoumarins from allyl esters. Kinetic and spectroscopic experiments support a mechanism in which the Lewis acidic gold complex catalyzes both an initial rearrangement step and a subsequent Lewis basic palladium oxidative-addition step.
Databáze: MEDLINE