Palladium catalysed cross-coupling of (fluoroarene)tricarbonylchromium(0) complexes

Abstract

Fluoroarenetricarbonylchromium(0) complexes were found to undergo Suzuki reactions with arylboronic acids to form biaryltricarbonylchromium(0) complexes in the presence of trimethylphosphine/palladium dibenzylideneacetone and caesium carbonate or caesium fluoride.

References

1. A. Suzuki, in Metal-catalyzed Cross-coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, p. 49.
2. K.-i. Gouda, E. Hagiwara, Y. Hatanaka and T. Hiyama, J. Org. Chem., 1996, 61, 7232.
3. W. J. Scott, J. Chem. Soc., Chem. Commun., 1987, 1755.
4. A. F. Littke and G. C. Fu, Angew. Chem., Int. Ed., 1998, 37, 3387.
5. D. W. Old, J. P. Wolfe and S. L. Buchwald, J. Am. Chem. Soc., 1998, 120, 9722.
6. F. Firooznia, C. Gude, K. Chan and Y. Satoh, Tetrahedron Lett., 1998, 39, 3985.
7. C. Zhang, J. Huang, M. L. Trudell and S. P. Nolan, J. Org. Chem., 1999, 64, 3804.
8. A. F. Little and G. C. Fu, Angew. Chem., Int. Ed., 1999, 38, 2413.
9. J. P. Gilday and D. A. Widdowson, J. Chem. Soc., Chem. Commun., 1986, 1235.
10. J. P. Gilday and D. A. Widdowson, Tetrahedron Lett., 1986, 27, 5525.
11. E.-I. Negishi and F. Liu, in Metal-catalyzed Cross-coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, p. 1.
12. K. Kirschke, J. Deutsch and H. J. Niclas, Phosphorus Sulfur Silicon Relat. Elem., 1996, 117, 293.
13. F. Rose-Munch, E. Rose, A. Semra, L. Mignon, J. Garcia-Oricain and C. Knobler, J. Organomet. Chem., 1989, 363, 297.
14. M. F. Semmelhack, G. Hilt and J. H. Colley, Tetrahedron Lett., 1998, 39, 7683.
15. V. V. Litvak, P. P. Kun and V. D. Shteingarts, Zh. Org. Khim., 1984, 20, 753.
16. F. E. Goodson, T. I. Wallow and B. M. Novak, J. Am. Chem. Soc., 1997, 119, 12 441.
17. M. Sakamoto, I. Shimizu and A. Yamamoto, Chem. Lett., 1995, 1101.
18. H. Yang, H. Gao and R. J. Angelici, Organometallics, 1999, 18, 2285.
19. M. F. Semmelhack, G. R. Clark, J. L. Garcia, J. J. Harrison, Y. Thebtaranonth, W. Wulff and A. Yamashita, Tetrahedron, 1981, 37, 3957.
20. Typical procedure: A solution of η⁶-(fluorobenzene)tricarbonylchro-mium(0)(0.300 g, 1.29 mmol), 4-methoxyphenylboronic acid (0.392 g, 2.58 mmol), caesium carbonate (0.925 g, 2.84 mmol), Pd₂(dba)₃(5 mol%, 0.060 g, 0.06 mmol) and PMe₃(20 mol%, 0.26 ml, 1 M solution in toluene) in deoxygenated DME (9 ml) was stirred under reflux for 16 h. Et₂O (50 ml) was added and the solution was washed with 10% aq. NaOH (15 ml), water (15 ml) and brine (15 ml) and dried over MgSO₄. Concentration in vacuo followed by column chromatography (eluent: 5% Et₂O-hexane) gave η⁶-(4′-methoxybiphenyl)tricarbonylchro-mium(0) as a yellow crystalline solid (0.360 g, 87%), mp 58–61 °C (Found: C, 59.99; H, 3.69. C₁₆H₁₂CrO₄ requires C, 60.01; H, 3.78%); V_max(KBr)/cm^–1 2986w, 2838w, 1977s, 1961s, 1887s, 1868s, 1609m, 1508m, 1454m, 1279m, 1249m, 1176m, 1020m, 840m, 819m, 661m, 629s, 535m; δ_H(270 MHz; CDCl₃) 7.43 (2H, d, J 8.9), 6.93 (2H, d, J 8.9), 5.64 (2H, dd, J 6.7, 1.0), 5.49 (2H, t, J 6.4), 5.28 (1H, tt, J 6.2, 1.0), 3.83 (3H, s); δ_C(68 MHz) 233.0, 160.4, 128.6, 128.3, 114.3, 111.2, 93.2, 91.6, 90.9, 55.4; m/z(EI) 320 (M⁺, 43%), 264 (39), 236 (93), 221 (11), 205 (5), 184 (9), 169 (4), 52 (100)(Observed: M⁺ 320.0141; C₁₆H₁₂CrO₄ requires 320.0130).