6533b82afe1ef96bd128cb40

RESEARCH PRODUCT

Efficient synthesis of racemic and chiral alkenyl sulfoxides by palladium-catalyzed Suzuki coupling

Ana Belen CuencaMercedes Medio-simónGisela ManchaNuria RodriguezGregorio Asensio

subject

Organic Chemistrychemistry.chemical_elementSulfoxideDABCOBiochemistryMedicinal chemistryCatalysischemistry.chemical_compoundchemistrySuzuki reactionDrug DiscoveryPalladium(II) acetateEnantiomeric excessPhosphinePalladium

description

Alkenyl sulfoxide derivatives are obtained in high yields through a palladium-catalyzed Suzuki/Miyaura cross-coupling reaction of racemic and chiral 1-halo sulfoxides with aryl and alkenyl boronic acids. Chiral substrates react with no loss of optical purity and high optical yields. The reaction takes place with different palladium catalysts, such as Pd(PPh 3 ) 4 or Pd(OAc) 2 /DABCO. Although nitrogen ligands like DABCO lead to an active palladium catalyst, they are less effective than the phosphine ones.

yearjournalcountryeditionlanguage
2010-08-01Tetrahedron
https://doi.org/10.1016/j.tet.2010.06.050