Vinylic Selenides

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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.


[edit] References

  1. Comasseto, J. V.; Ling, L. W.; Petragnani, N.; Stefani, H. A. Synthesis 1997, 373-403.
  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.
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