Journal of Organic Chemistry 2004-05-14

Synthesis of sulfoxides by the hydrogen peroxide induced oxidation of sulfides catalyzed by iron tetrakis(pentafluorophenyl)porphyrin: scope and chemoselectivity.

Enrico Baciocchi, Maria Francesca Gerini, Andrea Lapi

Index: J. Org. Chem. 10th ed., 69 , 3586-3589, (2004)

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Abstract

The oxidation of sulfides with H(2)O(2) catalyzed by iron tetrakis(pentafluorophenyl)porphyrin in EtOH is an efficient and chemoselective process. With a catalyst concentration 0.03-0.09% of that of the substrate, sulfoxides are obtained with yields generally around 90-95% of isolated product. With vinyl and allyl sulfides, no epoxidation is observed. With a catalyst concentration between 0.09% and 0.25% of that of the substrate, sulfones are obtained in almost quantitative yield and with the same high chemoselectivity observed in the synthesis of sulfoxides.