Biaryl formation: Palladium catalyzed cross-coupling reactions between hypervalent silicon reagents and aryl halides

Journal of Molecular Catalysis A: Chemical

Volumn 204-205, Issue , 2003, Pages 177-185

  Penso, M ^a   Albanese, D ^b   Landini, D ^b   Lupi, V ^b  

^a CNR   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

Cross coupling; Palladium catalyst; Pentacoordinated silicates; Phenylation; Quaternary onium salts

Indexed keywords

DIMERS; FLUORINE COMPOUNDS; PALLADIUM; SILANES; SOLVENTS;

CROSS-COUPLING REACTIONS;

CATALYSIS;

(TRIORGANO)SILANE; ALLYLPALLADIUM CHLORIDE; AROMATIC HALIDE; DIMER; DIMETHYL SULFOXIDE; ETHER DERIVATIVE; HALIDE; PALLADIUM; QUARTERNARY ONIUM HYDROGENDIFLUORIDE; QUATERNARY ONIUM TRIORGANO(DIFLUORO)SILICATE; SILICATE; SILICONE DERIVATIVE; SILYL ETHER; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CROSS COUPLING REACTION; HALOGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 18744438247     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1169(03)00297-8     Document Type: Article

References (54)

1. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 102 (2002) 1359.
2. A. Suzuki, in: F. Diederich, P.J. Stang (Eds.), Metal-catalyzed, Cross-coupling Reactions, Wiley-VCH, Weinheim, 1998 (Chapter 2).
3. N. Miyaura, A. Suzuki, Chem. Rev. 95 (1995) 2457.
4. T.N. Mitchell, in: F. Diederich, P.J. Stang (Eds.), Metal-catalyzed, Cross-coupling Reactions, Wiley-VCH, Weinheim, 1998 (Chapter 4).
5. J.K. Stille, A.M. Echavarren, R.M. Williams, J.A. Hendrix, Org. React. 71 (1992) 97.
6. A.G. Martìnez, J.O. Barcina, M. del Rosario Colorado Heras, A. de Fresno Cerezo, Org. Lett. 2 (2000) 1377.
7. A.G. Martìnez, J.O. Barcina, M. del Rosario Colorado Heras, A. de Fresno Cerezo, Organometallics 20 (2001) 1020, and references therein.
8. J.-L. Bréfort, R.J.P. Corriu, C. Guérin, B.J.L. Henner, W.W.C. Wo Chi Man, Organometallics 9 (1990) 2080, and references therein.
9. T. Hiyama, Y. Hatanaka, Pure Appl. Chem. 66 (1994) 1471.
10. Y. Hatanaka, T. Hiyama, Y. Synlett (1991) 845.
11. Y. Hatanaka, T. Hiyama, Tetrahedron Lett. 29 (1988) 97.
12. H. Matsuhashi, M. Kuroboshi, Y. Hatanaka, T. Hiyama, Tetrahedron Lett. 35 (1994) 6507.
13. T. Hiyama, H. Matsuhashi, A. Fujita, M. Tanaka, K. Hirabayashi, M. Shimizu, A. Mori, Organometallics 15 (1996) 5762.
14. Y. Hatanaka, K. Goda, Y. Okahara, T. Hiyama, Tetrahedron 50 (1994) 8301.
15. K. Gouda, E. Hagiwara, Y. Hatanaka, T. Hiyama, J. Org. Chem. 61 (1996) 7232.
16. Y. Hatanaka, T. Hiyama, J. Org. Chem. 53 (1988) 918.
17. Y. Hatanaka, T. Hiyama, J. Org. Chem. 54 (1989) 268.
18. K. Hirabayashi, A. Mori, J. Kawashima, M. Suguro, Y. Nishihara, T. Hiyama, J. Org. Chem. 65 (2000) 5342.
19. S.E. Denmark. J.Y. Choi, J. Am. Chem. Soc. 121 (1999) 5821.
20. S.E. Denmark, D. Wehrli, J.Y. Choi, Org. Lett. 2 (2000) 2491.
21. S.E. Denmark, D. Wehrli, Org. Lett. 2 (2000) 565.
22. S.E. Denmark, L. Neuville, Org. Lett. 2 (2000) 3221.
23. S.E. Denmark, R.F. Sweis, J. Am. Chem. Soc. 123 (2001) 6439.
24. S.E. Denmark, Z. Wu, Org. Lett. 1 (1999) 1495.
25. S.E. Denmark, Z. Wang, J. Organomet. Chem. 624 (2001) 372.
26. S.E. Denmark, S.-M. Yang, Org. Lett. 3 (2001) 1749.
27. S.E. Denmark, S.-M. Yang, J. Am. Chem. Soc. 124 (2002) 2102.
28. M.E. Mowery, P. DeShong, J. Org. Chem. 64 (1999) 1684.
29. M.E. Mowery, P. DeShong, Org. Lett. 1 (1999) 2137.
30. P.Y.S. Lam, S. Deudon, K.M. Averill, R. Li, M.Y. He, P. DeShong, C.G. Clark, J. Am. Chem. Soc. 122 (2000) 7600.
31. R. Correia, P. DeShong, J. Org. Chem. 66 (2001) 7159.
32. A.S. Pilcher, H.L. Hammon, P. DeShong, J. Am. Chem. Soc. 117 (1995) 5166.
33. A.S. Pilcher, P. DeShong, J. Org. Chem. 61 (1996) 6901.
34. M.-R. Brescia, P. DeShong, J. Org. Chem. 63 (1998) 3156.
35. M.E. Mowery, P. DeShong, J. Org. Chem. 64 (1999) 3266.
36. S. Yamasaki, K. Fujii, R. Wada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 124 (2002) 6536.
37. D. Albanese, D. Landini, M. Penso, Tetrahedron Lett. 36 (1995) 8865.
38. D. Albanese, D. Landini, M. Penso, S. Petricci, Synlett (1999) 199.
39. C.J. Handy, Y.F. Lam, P. DeShong, J. Org. Chem. 65 (2000) 3542.
40. Dictionary of Organic Compounds, vol. 1, fifth ed., Chapmann & Hall, New York, 1982, p. 672.
41. Dictionary of Organic Compounds, vol. 4, fifth ed., Chapmann & Hall, New York, 1982, p. 4236.
42. Dictionary of Organic Compounds, vol. 2, fifth ed., Chapmann & Hall, New York, 1982, p. 2260.
43. Dictionary of Organic Compounds, vol. 4, fifth ed., Chapmann & Hall, New York, 1982, p. 3935.
44. Dictionary of Organic Compounds, vol. 5, fifth ed., Chapmann & Hall, New York, 1982, p. 4643.
45. Dictionary of Organic Compounds, vol. 5, fifth ed., Chapmann & Hall, New York, 1982, p. 4643.
46. Dictionary of Organic Compounds, vol. 1, fifth ed., Chapmann & Hall, New York, 1982, p. 31.
47. R.C. Fuson, R.L. Talbott, J. Org. Chem. 26 (1961) 2674.
48. J.-J. Godfroid, Bull. Soc. Chim. Fr. (1964) 2929.
49. D. Landini, H. Molinari, M. Penso, A. Rampoldi, Synthesis (1988) 953.
50. C. Chuit, R.J.P. Corriu, C. Reye, J.C. Young, Chem. Rev. 93 (1993) 1371.
51. R.J.P. Corriu, J. Organomet. Chem. 400 (1990) 81.
52. J. Kvíèala, P. Mysík, O. Paleta, Synlett (2001) 547.
53. C. Mateo, C. Fernández-Rivas, A.M. Echavarren, D.J. Cárdenas, Organometallics 16 (1997) 1997.
54. J.P. Collman, L.S. Hegedus, J.R. Norton, R.G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, 1987, p. 884, and references therein.