Palladium-catalyzed cross-coupling of silanols, silanediols, and silanetriols promoted by silver(I) oxide

Journal of Organic Chemistry

Volumn 65, Issue 17, 2000, Pages 5342-5349

  Hirabayashi, Kazunori ^a   Mori, Atsunori ^a   Kawashima, Jun ^a   Suguro, Masahiro ^a   Nishihara, Yasushi ^a   Hiyama, Tamejiro ^a,b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; SILANE DERIVATIVE; SILVER DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; X RAY DIFFRACTION;

EID: 0034714410     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000679p     Document Type: Article

References (54)

1. For a review on silanol: Lickiss, P. D. Adv. Inorg. Chem. 1995, 42, 147-262.
2. (a) Hirabayashi, K.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1997, 38, 461-464.
3. (b) Hirabayashi, K.; Takahisa, E.; Nishihara, Y.; Mori, A.; Hiyama, T. Bull, Chem. Soc. Jpn. 1998, 71, 2409-2417.
4. (a) Chan, T. H.; Chen, L. M.; Wang, D. J. Chem. Soc., Chem. Commun. 1988, 1280-1281.
5. (b) Chan, T. H.; Chen, L. M.; Wang, D.; Li, L. H. Can. J. Chem. 1993, 71, 60-67.
6. (c) Yamamoto, K.; Kawanami, Y.; Miyazawa, M. J. Chem. Soc., Chem. Commun. 1993, 436-437.
7. (d) Li, L. H.; Chan, T. H. Tetrahedron Lett. 1997, 38, 101-104.
8. (a) Takaku, K.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1997, 38, 5189-5192.
9. (b) Uehira, S.; Takaku, K.; Shinokubo, H.; Oshima, K. Synlett 1998, 1096-1098.
10. Trost, B. M.; Ito, N.; Greenspan, P. D. Tetrahedron Lett. 1993, 34, 1421-1424.
11. (a) Takaku, K.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1996, 37, 6781-6784.
12. (b) Shinokubo, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1997, 70, 2255-2263.
13. (a) Hoveyda, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370.
14. (b) Snieckus, V. Chem. Rev. 1990, 90, 879-933.
15. (a) Hirabayashi, K.; Nishihara, Y.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1998, 39, 7893-7896.
16. See also: (b) Hirabayashi, K.; Ando, J.; Mori, A.; Nishihara, Y.; Hiyama, T. Synlett 1999, 99-101.
17. (c) Hirabayashi, K.; Ando, J.; Kawashima, J.; Nishihara Y.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 1409-1417.
18. (a) Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1471-1478.
19. (b) Hiyama, T. Organosilicon Compounds in Cross-Coupling Reactions. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P., Eds.; Wiley-VCH: 1998; Chapter 10, pp 421-454.
20. See also: (c) Mowery, M. E.; DeShong, P. J. Org. Chem. 1999, 64, 1684-1688.
21. (d) Denmark, S. E.; Choi, J. Y. J. Am. Chem. Soc. 1999, 121, 5821-5822.
22. (e) Denmark, S. E.; Wu, Z. Org. Lett. 1999, 1, 1495-1498.
23. The preliminary communication: Hirabayashi, K.; Kawashima, J.; Nishihara, Y.; Mori, A.; Hiyama, T. Org. Lett. 1999, 1, 299-301.
24. Denmark independently reported the cross-coupling of alkenyl-silanols using a fluoride ion as an activator: Denmark, S. E.; Wu, Z. Org. Lett. 2000, 2, 565-568.
25. (a) Hatanaka, Y.; Fukushima, S.; Hiyama, T. Chem. Lett, 1989, 1711-1714.
26. (b) Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1989, 54, 268-270.
27. 20 has been used as an activator in the cross-coupling reactions of organoboron and organosilicon compounds: (a) Uenishi, J.; Beau, J.-M.; Armstrong, R. W.; Kishi, Y. J. Am. Chem. Soc. 1987, 109, 4756-4758.
28. (b) Gillmann, T.; Weeber, T. Synlett 1994, 649-650.
29. (c) Malm, J.; Björk, P.; Gronowitz, S.; Hörnfeldt, A.-B. Tetrahedron Lett. 1992, 33, 2199-2202.
30. (d) Mateo, C.; Ferández-Rivas, C.; Echavarren, A. M.; Cárdenas, D. J. Organometallics 1997, 16, 1997-1999.
31. Ito, Y.; Konoike, T.; Saegusa, T. J. Am. Chem. Soc. 1975, 97, 649-651.
32. Such difference of the reactivity was also shown in the reactions of aryl- and alkenylsilacyclobutanes. See ref 9d,e.
33. (a) George, P. D.; Sommer, L. H.; Whitmore, F. C. J. Am. Chem. Soc. 1963, 75, 1585-1588.
34. (b) Takiguchi, T. J. Am. Chem. Soc. 1959, 81, 2359-2361.
35. Barnes, G. H., Jr.; Daughenbaugh, N. E. J. Org. Chem. 1966, 31, 885-887.
36. See the Supporting Information.
37. A cross-coupling reaction with chlorosilanes in the presence of NaOH might also be formation of oligosiloxanes. See: Gouda, K.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232-7233.
38. 2O afforded 3a in 43% yield.
39. We also confirmed the formation of disiloxane in the coupling of 2-phenylethynyl(diniethyl)phenylsilane with an aryl iodide to give the corresponing coupling product along with 1,1,3,3-tetramethyl-1,3-diphenyldisiloxane in an excellent yield: Hirabayashi, K.; Kawashima, J.; Mori, A. Unpublished results.
40. 2O is known to serve as an activator in the Williamson ether synthesis, the reaction of alcohol with alkyl iodide. See: Walker, H. G., Jr.; Gee, M.; McCready, R. M. J. Am. Chem. Soc. 1962, 27, 2100-2102.
41. Halide abstraction by silver salt from arylpalladium halide to give cationic palladium species. For example, see: Grove, D. M.; van Koten, G.; Louwen, J. N.; Noltes, J. G.; Spec, A. L. J. Am. Chem. Soc. 1982, 104, 6609-6616.
42. Although aryl bromide or triflate is less reactive in the oxidative addition by Pd(0), such a drastic change in the yield (52% vs trace) seems unlikely.
43. Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434-5444.
44. Wallow, T. I.; Novak, B. M. J. Org. Chem. 1994, 59, 5034-5037.
45. Brune, H. A.; Stapp, B.; Schmidtberg, G. J. Organomet. Chem. 1986, 507, 129-137.
46. Kelkar, A. A.; Hanaoka, T.; Kubota, Y.; Sugi, Y. Catal. Lett. 1994, 29, 69-75.
47. Li, G. M.; Kamogawa, T.; Segi, M.; Nakajima, T. Chem. Express 1993, 8, 53-56.
48. Maccarone, E.; Mamo, A.; Perrini, G.; Torre, M. J. Chem. Soc., Perkin Trans. 2 1981, 324-326.
49. Fukuzawa, S.; Tsuchimoto, T.; Hiyama, T. J. Org. Chem. 1997, 62, 151-156.
50. Harris, G. J. Chem. Soc. B 1970, 488-491.
51. Cacchi, S.; Felici, M.; Pietroni, B. Tetrahedron Lett. 1984, 25, 3137.
52. Negishi, E.; Takahashi, T.; Baba, S.; Van Horn, D. E.; Okukado, N. J. Am. Chem. Soc. 1987, 709, 2393-2401.
53. Duboudin, J. G.; Jousseaume, B. J. Organomet. Chem. 1978, 162, 209.
54. XRD pattern of AgI is available form International Centre for Diffraction Data HCDD).