Potassium vinyltrifluoroborate: A stable and efficient vinylating agent of arenediazonium salts using palladium catalysts

Tetrahedron Letters

Volumn 39, Issue 28, 1998, Pages 5045-5048

  Darses, Sylvain ^a   Michaud, Guillaume ^a   Genêt, Jean Pierre ^a  

^a Lab de Synt Selective Organique   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; MOLECULAR INTERACTION; MOLECULAR STABILITY; SYNTHESIS;

EID: 0032500090     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01003-X     Document Type: Article

References (21)

1. 1. For recent books see : (a) Tsuji, J. Palladium Reagents and Catalysts, Wiley & sons, 1995 ;
2. (b) Malleron, J.L.; Fiaud, J.C.; Legros, J.Y. Handbook of Palladium-Catalyzed Organic Reactions, Academic Press, London, 1997.
3. For recent reviews see : (a) Heck, R.F. in Comprehensive Organic Synthesis, Oxford, Pergamon Press, 1991;
4. (b) De Meijere, A.; Meyer, F.E. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411 ;
5. (c) Negishi, E.; Coperet, C.; Ma S.; Liou, S.Y.; Liu, F. Chem. Rev. 1996, 365-393 ;
6. (d) Bräse, S.; De Meijere, A. Metal-Catalyzed Cross-Coupling Reactions, Eds. Stang, P.J.; Diederich, F. Wiley-VCH, Weiheim, 1997.
7. 2. Review : Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
8. 3. (a) Darses, S.; Jeffery, T.; Brayer, J.L.; Demoute, J.P.; Genêt, J.P. Tetrahedron Lett. 1996, 37, 3857-3860.
9. (b) Darses, S.; Jeffery, T.; Brayer, J.L.; Demoute, J.P.; Genêt, J.P. Bull. Soc. Chim. Fr. 1996, 133, 1095-1102.
10. 4. Sengupta, S.; Bhattacharyya, S. J. Org. Chem. 1997, 62, 3405-3406.
11. 5. Darses, S.; Brayer, J.L.; Demoute, J.P.; Genêt, J.P. Tetrahedron Lett. 1997, 38, 4393-4396.
12. 6. Darses, S. PHD Thesis University P. M. Curie, December 1997.
13. 7. Vedejs, E.; Chapman, R.W.; Fields, S. C.; Lin, S.; Schrimpf, M.R. J. Org. Chem. 1995, 60, 3020-3027.
14. 8. Hunt, A.R.; Stewart, S.K.; Whiting, A. Tetrahedron Lett. 1993, 34, 3599-3602.
15. 9. Potassium vinyltrifluoroborate 1 : To a solution of trimethylborate (freshly distilled over sodium, 34 ml, 1.5 eq.) in anhydrous THF (200 ml) was added dropwise a 15% solution of vinylmagnesium chloride in THF (119 ml, 0.2 mol) at -60°C. The mixture was stirred under argon for 30 min at -60°C, placed at room temperature and stirred another 30 min. Potassium hydrogen difluoride (94 g, 6 eq.) was added at once at 0°C followed by slow addition of water (200 ml) which resulted in an intense white precipitate. The suspension was stirred 30 mn at room temperature and the solvents were removed under (bath temperature : 50°C). The resulting powder was thoroughly dried under vacuum (< 1 mmHg) overnight, extracted several times with acetone (3×150 ml) and the solvent removed under vacuum. The product was purified by dissolving in the minimum amount of boiling acetone and reprecipitation by addition of diethyl ether. 22.53 g of potassium vinyltrifluoroborate were obtained as a white powder (84% yield). This material has been prepared for the first time (Stafford, S.L. Can. J. Chem. 1963, 41, 807-808) in a two step sequence from tetravinylstannane in 29% yield.
16. 10. Herrmann, W.A.; Brossmer, C.; Öfele, K.; Reisinger, C.P.; Priermeier, T.; Beller, M.; Fisher, H. Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1848.
17. 10 (0.1 to 5 mol%) were placed in a flask under an argon atmosphere, in the dark (aluminium foil). Degassed methanol (10 ml) were then added and the resulting suspension was stirred at 20°C for the indicated time. The course of the coupling was followed by measuring gas evolution with a gas buret. After completion, the mixture was filtered off on celite and washed with diethyl ether. The organic phase was washed several times with brine and dried over anhydrous magnesium sulfate. The solvent was removed and the crude product was purified by Kugelrohr distillation.
18. 12. Until now the most useful, vinyltributylstannane has been developed by Stille et al. (a) McKean, D.R.; Parrinello, G.; Renaldo, A.F.; Stille, J.K. J. Org. Chem. 1987, 52, 422-424.
19. (b) Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478-5486.
20. (c) Roth, G.P.; Fuler, C.E. J. Org. Chem. 1991, 56, 3493-3496.
21. (d) Badone, D.; Cecchi, R.; Guzzi, U. J. Org. Chem. 1992, 57, 6321-6323. However such coupling are generally limited to the rather expensive aryl iodide, bromide and triflate and toxic side products are formed in this reaction.