Sulfoxides are known for their utility in organic synthesis, as ligands for transition metal catalysis, and for their bioactivities. Alpha-arylation of unactivated sulfoxides, unlike alpha-arylation of carbonyl compounds, is unknown, probably because of the high pKa of the sulfoxides alpha-hydrogens. In this work, an effective palladium catalyst system for the direct arylation of aryl methyl sulfoxides with aryl halides has been developed. The optimization of the reaction was guided by High Throughput Experimentation (HTE). It was observed that the yield greatly depends upon how the palladium complex was generated. This method could be utilized in the synthesis of natural products or bioactive compounds containing the aryl benzyl sulfoxides substructure.

Palladium-catalyzed direct arylation of aryl methyl sulfoxides with aryl halides

244th National Meeting (2012)

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