Cross-coupling reactions of arenediazonium tetrafluoroborates with potassium aryl- or alkenyltrifluoroborates catalyzed by palladium

Tetrahedron Letters

Volumn 38, Issue 25, 1997, Pages 4393-4396

  Darses, Sylvain ^a   Genêt, Jean Pierre ^a   Brayer, Jean Louis ^b   Demoute, Jean Pierre ^b  

^a CNRS   (France)

^b SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOBORON DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; REACTION ANALYSIS;

EID: 0030900078     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00939-8     Document Type: Article

References (20)

1. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. For examples of this cross-coupling reaction in aqueous medium see :
2. (b) Casalnuovo, A. L.; Calabrese, J. C. J. Am. Chem. Soc. 1990, 112, 4324-4330.
3. (c) Genêt, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717.
4. (d) Genêt, J. P.; Lindquist, A.; Blart, E.; Mouries, V.; Savignac, M.; Vaultier, M. Tetrahedron Lett. 1995, 36, 1443-1446.
5. (a) Darses, S.; Jeffery, T.; Brayer, J. L.; Demoute, J. P.; Genêt, J. P. Tetrahedron Lett. 1996, 37, 3857-3860.
6. (b) Darses, S.; Jeffery, T.; Brayer, J. L.; Demoute, J. P.; Genêt, J. P. Bull. Soc. Chim. Fr 1996, 133, 1095-1102.
7. In many Suzuki cross-coupling reactions, the organoborate, formed by the reaction of the corresponding boron reagent with a base or other nucleophiles such as fluoride, can be considered as the actual nucleophile : (a) Fürstner, A.; Seidel, G. Tetrahedron 1995, 51, 11165-11176.
8. (b) Smith, G. B.; Denezy, G. C.; Hughes, D. L.; King, A. O.; Verhoeven, T. R. J. Org. Chem. 1994, 59, 8151-8156.
9. (c) Aliprantis, A. O.; Canary, J. W. J. Am. Chem. Soc. 1994, 116, 6985-6986.
10. (d) Wright, S. W.; Hageman, D. L.; McClure, L. D. J. Org. Chem. 1994, 59, 6095-6097.
11. Vedejs, E.; Chapman, R. W.; Fields, S. C.; Lin, S.; Schrimpf, M. R. J. Org. Chem. 1995, 60, 3020-3027.
12. (a) Chambers, R. D.; Clark, H. C.; Willis, C. J. J. Am. Chem. Soc. 1960, 82, 5298-5301.
13. (b) Stafford, S. L. Can. J. Chem. 1963, 41, 807-808.
14. (c) Chambers, R. D.; Chivers, T.; Pyke, D. A. J. Chem. Soc. 1965, 5144-5145.
15. 2 (3.3 equivalents). The resulting suspension was stirred 10 minutes and the solvent was removed in vacuo. The solid was extracted with several portions of acetone and the solvent was removed to afford crude potassium organotrifluoroborate. It was then purified by recristallisation or reprecipitation from acetone/diethyl ether. Yields of purified products were generally over 95%. Potassium vinyltrifluoroborate was prepared analogously from the commercially available 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane (Acros Organics).
16. 2 (5 mol%) were mixed under an argon atmosphere, in a foil covered flask. Anhydrous 1,4-dioxane (4 ml) was then added and the resulting suspension stirred at 20°C for the indicated time. The course of the reaction was followed by measuring gas evolution with a gas buret. After completion, the reaction mixture was diluted with diethyl ether, washed several times with brine and dried over anhydrous magnesium sulphate. The solvent was then removed and the crude product purified by column chromatography on silica gel.
17. 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. Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem. Int. Ed. Engl. 1995, 34, 1848-1849.
18. 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. Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem. Int. Ed. Engl. 1995, 34, 1848-1849.
19. CF = 22 Hz).
20. In the case of 4-iodobenzenediazonium tetrafluoroborate, an analysis (GC/MS, column DB-1701, J&W Scientific) of the crude product revealed the presence of 4-5% of [1,1′;4′,1″]terphenyl.