Efficient one-pot conversion of carbonyl compounds to their alpha,beta-unsaturated derivatives using a recoverable, minimally fluorous organoselenium reagent
A protocol for the preparation of a fluorous arylselenenyl chloride is described. This selenenyl chloride may be used for the direct alpha-selenation of ketones and, following oxidation and syn-elimination, formation of alpha,beta-unsaturated carbonyl compounds. Treatment of the crude reaction mixtures with sodium metabisulfite reduces the various selenium species to the diaryl diselenide, which is then recovered in high yield by continuous fluorous extraction.
Crich
D
Department of Chemistry, University of Illinois at Chicago 60607-7061, USA. dcrich@uic.edu
Barba
GR