Efficient synthesis of racemic and chiral alkenyl sulfoxides by palladium-catalyzed Suzuki coupling
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(PPh3)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.
Mancha, Gisela,Cuenca, Ana B.,Rodríguez, Nuria,Medio-Simón, Mercedes,Asensio, Gregorio
experimental part
p. 6901 - 6905
(2010/09/18)
Optically active sulfoxides by enantiospecific reactions of bromovinyl aryl sulfoxides with grignard reagents
Optically active bromovinyl aryl sulfoxides were subjected to reactions with phenyl- or alkyl-magnesium compounds, with the production of optically active diaryl or aryl alkyl sulfoxides, with inversion of configuration. The enantiospecificity of the process was found to be 98-100%.
Cardellicchio, Cosimo,Fiandanese, Vito,Naso, Francesco,Scilimati, Antonio
p. 5121 - 5124
(2007/10/02)
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