Vinylic Selenides

Vinylic selenides play an important role in the synthesis of organoselenium compounds, especially in the development of many convenient methods for the stereoselective preparation of functionalized alkenes.¹ Although various methods are mentioned for the preparation of vinylic selenides, a more useful procedure has centered on the nucleophilic or electrophilic organoselenium addition to terminal or internal alkynes.² For example, the nucleophilic addition of senophenol to alkynes affords, preferentially, the Z-vinylic selenides after longer reaction times at room temperature.The reaction is faster at a high temperature; however, the mixture of Z- and E-vinylic selenides was obtained in an almost 1:1 ratio.³ On the other hand, the adducts, depending on the nature of the substituents at the triple bond. Conversely, vinylic selenides can be prepared by palladium-catalyzed hydroselenation of alkynes to afford the Markownikov adduct in good yields. There are some limitations associated with the methodologies to prepare vinylic selenides illustrated above; procedures described employ diorganoyl diselenides or selenophenol as starting materials, which are volatile and unstable and have an unpleasant odor. Also, the preparation of these compounds is complex.

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References

1. (a) Comasseto, J. V.; Ling, L. W.; Petragnani, N.; Stefani, H. A. Synthesis 1997, 373-403. (b) Zeni, G.; Stracke, M. P.; Lissner, E.; Braga, A. L. Synlett 2003, 12, 1880-1882.
2. (a) Comasseto, J. V. J. Organomet. Chem. 1983, 253, 131-181. (b) Zeni, G.; Stracke, M. P.; Nogueira,C. W.; Braga,A. L.; Menezes,P. H.; Stefani H. A. Organic Letters 2004, 6, 1135-1138. (c) Dabdoub, M. J.; Dabdoub, V.B.; Pereira, M. A. Tetrahedron Lett. 2001, 42, 1595-1597. (d) Dabdoub,M. J.; Baroni, A. C. M.; Lenardão, E. J.; Gianeti, T. R.; Hurtado, G. R.Tetrahedron 2001, 57, 4271-4276. (e) Dabdoub, M. J.; Cassol, T. M.;Batista, A. C. F. Tetrahedron Lett. 1996, 37, 9005-9008. (f) Barros, O. S. D.; Lang, E. S.; de Oliveira, C. A. F.; Peppe, C.; Zeni, G.Tetrahedron Lett. 2002, 43, 7921-7923.
3. Comasseto, J. V.; Ferreira, J. T. B. J. Organomet. Chem. 1981, 216,287-294.