A practical catalytic method for the preparation of steroidal 1,4-dien-3-ones by oxygen atom transfer from iodoxybenzene to diphenyl diselenide

Abstract

The dehydrogenation of steroidal 3-ketones can be accomplished in high yield using benzeneseleninic anhydride generated in situ by efficient oxygen atom transfer from iodoxybenzene to catalytic amounts of diphenyl diselenide. An experimentally convenient and economical development of this catalytic cycle is the use of meta-iodoxybenzoic acid which both avoids chromatography and allows recovery of meta-iodobenzoic acid and diphenyl diselenide. 12-Hydroxy- and 12-keto-steroids are also dehydrogenerated very efficiently using this catalytic process.