Portal de Periódicos da CAPES

Catalyzed Catalysis Using Carbophilic Lewis Acidic Gold and Lewis Basic Palladium: Synthesis of Substituted Butenolides and Isocoumarins

2009; American Chemical Society; Volume: 131; Issue: 50 Linguagem: Inglês

10.1021/ja9068497

1943-2984

Yili Shi, Katrina E. Roth, Stephen D. Ramgren, Suzanne A. Blum,

Oxidative Organic Chemistry Reactions

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.