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

Gisela Mancha, Ana B. Cuenca, Nuria Rodríguez, Mercedes Medio-Simón, Gregorio Asensio

Research output: Indexed journal article Articlepeer-review

5 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)6901-6905
Number of pages5
JournalTetrahedron
Volume66
Issue number34
DOIs
Publication statusPublished - 21 Aug 2010
Externally publishedYes

Keywords

  • Boronic acids
  • Cross-coupling
  • Palladium
  • Sulfoxides
  • Suzuki reaction

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