Regio- and stereochemical aspects of the palladium-catalyzed desilylation-arylation of substituted vinylsilanes

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 7139-7146

  Alvisi, Davide ^a   Blart, Errol ^b   Bonini, Bianca Flavia ^a   Mazzanti, Germana ^a   Ricci, Alfredo ^a   Zani, Paolo ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b Centre National de la Recherche Scientifique   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000494782     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960301k     Document Type: Article

References (36)

1. Colvin, E. W. Silicon in Organic Synthesis; Butterworth: London, 1981.
2. (a) Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: Berlin, 1983.
3. (b) Hudrlik, P. F.; Hudrlik, A. M.; Kulkarni, A. K. J. Am. Chem. Sac. 1985, 107, 4260.
4. For leading references regarding the electrophilic substitution reactions of vinylsilanes, see: (a) Chan, T. H.; Fleming, I. Synthesis 1979, 761. (b) Magnus, P. Aldrichimica Acta 1980, 13, 41.
5. For leading references regarding the electrophilic substitution reactions of vinylsilanes, see: (a) Chan, T. H.; Fleming, I. Synthesis 1979, 761. (b) Magnus, P. Aldrichimica Acta 1980, 13, 41.
6. (a) Fry, Y. L.; Mc Adam, M. A. Tetrahedron Lett. 1984, 25, 5859.
7. (b) Furin, G. G.; Vyazankina, O. A.; Gostevsky, B. A.; Vyazankin, N. S. Tetrahedron 1988, 44, 2675 and references therein.
8. (a) Kochi, J. K. Organometallic Mechanisms and Catalysis; Academic Press: New York, 1987.
9. (b) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985.
10. (c) Davies, S. G. Organotransition Metal Chemistry. Application to Organic Synthesis; Pergamon Press: Oxford, 1982.
11. (d) Hegedus, L. S. Organometallics in Synthesis; John Wiley & Sons Ltd: Chichester, UK, 1994.
12. (e) Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1988, 53, 918 and references therein.
13. For reviews, see: (a) Stille, J. K. Angew. Chem. Int. Ed. Engl. 1986, 25, 508. (b) Mitchell, T. N. Synthesis 1992, 803.
14. For reviews, see: (a) Stille, J. K. Angew. Chem. Int. Ed. Engl. 1986, 25, 508. (b) Mitchell, T. N. Synthesis 1992, 803.
15. Hallberg, A.; Westerlund, C. Chem. Lett. 1982, 1993.
16. (a) Karabelas, K.; Westerlund, C.; Hallberg, A. J. Org. Chem. 1985, 50, 3896.
17. (b) Karabelas, K.; Hallberg, A. J. Org. Chem. 1986, 51, 5286.
18. Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1471 and references therein.
19. (a) Capella, L.; Degl' Innocenti, A.; Reginato, G.; Ricci, A.; Taddei, M. J. Org. Chem. 1989, 54, 1473.
20. (b) Casarini, A.; Jousseaume, B.; Lazzari, D.; Porciatti, E.; Reginato, G.; Ricci, A.; Seconi, G. Synlett 1992, 981.
21. (c) Capella, L.; Capperucci, A.; Curotto, G.; Lazzari, D.; Dembech, P.; Reginato, G.; Ricci, A. Tetrahedron Lett. 1993, 34, 3311.
22. Heck, R. F.; Nolley, J. P., Jr. J. Org. Chem. 1972, 37, 2320.
23. Heck, R. F. Acc. Chem. Res. 1979, 12, 146 and references therein.
24. Mc Crindle, R.; Ferguson, G.; Khan, M. A.; Mc Alees, A. J.; Ruhl, B. L. J. Chem. Soc. Dalton Trans. 1981, 986.
25. Cabri, W.; Candiani, I.; Bedeschi, A. J. Org. Chem. 1992, 57, 3558.
26. Henry, P. M. Palladium Catalyzed Oxidation of Hydrocarbons; D. Riedel: Dordrecht, Holland, 1980, pp 11-15.
27. Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S. J. Org. Chem. 1992, 57, 1481.
28. Jarvie, A. W. Organomet. Chem. Rev., Sect. A 1970, 6, 153.
29. Larhed, M.; Andersson, C.-M.; Hallberg, A. Tetrahedron 1994, 50, 285.
30. Larhed, N.; Andersson, C.-M.; Hallberg, A. Acta Chem. Scand. 1993, 47, 212
31. Genet, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715.
32. Cacchi, S.; Arcadi, A. J. Org. Chem. 1983, 48, 4236.
33. (a) Denmark, S. E.; Amburgey J. J. Am. Chem. Soc. 1993, 115, 10386.
34. (b) Cretan, I.; Marek, I.; Brasseur, D.; Jestin, J.-L.; Normant, J.-F. Tetrahedron Lett. 1994, 35, 6973.
35. Hudrlik, P. F.; Waugh, M. A.; Hudrlik, A. M. J. Organomet. Chem. 1984, 271, 69.
36. Fleming, I.; Newton, T. W.; Roessler, F. J. Chem. Soc. Perkin Trans. 1 1981, 2527.