Regioselective Synthesis of Conjugated Dienones

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  • Published: 10 February 2019
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Organic Letters/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Regioselective Synthesis of Conjugated Dienones

Sulfoxonium ylides can serve as carbene precursors in organic reactions. The can be used as safer alternatives to diazo compounds in this role.

Huanfeng Jiang, South China University of Technology, Guangzhou, and Lanzhou University, both China, and colleagues have developed a synthesis route to conjugated dienones (pictured) which is based on a palladium-catalyzed reaction between sulfoxonium ylides and allylarenes. The team reacted a variety of these substrates in the presence of Pd(OAc)2 as a catalyst, 2,6-dimethylcyclohexa-2,5-diene-1,4-dione (DMBQ) as an oxidant, and PPh3 as a ligand in dimethylsulfoxide (DMSO).

The desired conjugated dienones were obtained in moderate to good yields and with good regioselectivity. The reaction tolerates a range of functional groups and can be performed on a gram scale. According to the researchers, the method could be useful for the synthesis of bioactive molecules.


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