A mild, osmium tetraoxide-catalyzed method for the oxidation of sulfides to sulfones

✍ Scribed by Stephen W. Kaldor; Marlys Hammond

• Book ID: 104225821
• Publisher: Elsevier Science
• Year: 1991
• Tongue: French
• Weight: 214 KB
• Volume: 32
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)93423-3

✦ Synopsis

Osmium tetraoxide has been demonstrated to be a highly efficient catalyst for the chemoselective oxidation of a variety of sulfides to the corresponding sulfones. Tertiary amine catalysis appears to play a key role in the reaction.

Although considerable effort has been expended on the development of methods for the oxidation of sulfides to sulfones,1 mild, chemoselective procedures for effecting this transformation are relatively scarce.

We now wish to report that osmium tetraoxide is a selective and highly efficient catalyst for performing this oxidation. In the presence of the co-oxidant N-methylmorpholine-N-oxide (NMO), one mole percent of catalyst is sufficient to oxidize a variety of sulfides to the corresponding sulfones in nearly quantitative yields. This room temperature oxidation method is tolerant of a number of other functional groups: chemoselective oxidation of a sulfide in the presence of an olefin is even possible in some instances.