Synthesis of Vinyl Selenides

Several developments made in the field of new, improved chemoselective and regioselective methods for the synthesis of vinyl selenides, was reported. Silveira and colleagues have described the preparation of functionalized vinyl selenides by the Horner reaction. Thus, the reaction of cyanomethylphosphonate with phenylselenenyl chloride, followed by reaction with aromatic and aliphatic aldehydes under basic conditions, afforded α-phenylselenoacrylonitriles in 58-92% yields. Murai and colleagues described the aldol-type condensation reaction of selenothioacetic acid S-butyl ester with aldehydes, followed by treatment with methyl iodide, to afford a mixture of (E) and (Z) ketene selenothioacetals. The hydrozirconation of internal acetylenic selenides and tellurides can be used for the preparation of several functionalized vinyl selenides and ketone selenochalcogenoacetals. Tieco and co-workers prepared several protected hydroxyl-(Z)-α-(phenylseleno)vinyl p-toluenesulfonates from the treatment of alkynyl phenylselenides.