6533b7dcfe1ef96bd1271fb7

RESEARCH PRODUCT

First Synthesis of β-Keto Sulfoxides by a Palladium-Catalyzed Carbonylative Suzuki Reaction

Cristian MollarNuria RodríguezGregorio AsensioMercedes Medio-simón

subject

inorganic chemicalsArylOrganic Chemistrychemistry.chemical_elementSulfoxideGeneral MedicineBiochemistryMedicinal chemistryCatalysischemistry.chemical_compoundchemistrySuzuki reactionOrganic chemistryPhysical and Theoretical ChemistryCarbonylationCarbon monoxidePalladium

description

[reaction: see text] An unprecedented palladium-catalyzed three-component cross-coupling reaction between alpha-bromo sulfoxide, carbon monoxide, and aromatic boronic acids provides a new and efficient approach to the synthesis of beta-ketosulfoxides. The reaction takes place under mild conditions with a wide range of variously substituted aryl and heteroaryl boronic acids. The carbonylative cross-coupling reaction is strongly favored over competing direct cross-coupling and homocoupling processes, except with boronic acids carrying strong electron-withdrawing substituents.

https://doi.org/10.1021/ol0518737