Efficient synthesis of arylsilanes by Cross-coupling of aromatic compounds with hydrosilanes as silicon sources

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 67, Issue 8, 2009, Pages 778-786

  Yamanoi, Yoshinori ^a   Nishihara, Hiroshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Arylation; Arylsilanes; Carbon hydrogen bond activation; Cross coupling; Hydrosilanes; Organometallic reagents; Silicon carbon bond formation; Transition metal catalysts

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; CATALYSTS; CHEMICAL REACTIONS; HYDROGEN BONDS; HYDROSILYLATION; ORGANOMETALLICS; SILICON; TRANSITION METALS;

ARYLATIONS; ARYLSILANES; CARBON-HYDROGEN BOND; CROSS-COUPLINGS; HYDROSILANES; ORGANOMETALLIC REAGENT; SILICON CARBON BOND; TRANSITION METAL CATALYSTS;

SILICON COMPOUNDS;

EID: 72449174795     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.67.778     Document Type: Article

References (80)

1. (a) J. F. Hartwig, Pure Appl. Chem., 71, 1417 (1999);
2. (b) I. P. Beletskaya, ibid., 77, 2021 (2005);
3. (c) J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev., 102,1359 (2002);
4. (d) "Metal-Catalyzed Cross-Coupling Reactions, 2nd ed." eds., by A: de Meijere, F. Diederich, Wiley-VCH, Weinheim, 2004;
5. (e) J. Tsuji, "Palladium Reagents and Catalysts", John Wiley & Sons, Chichester, 2004;
6. (f) D. Prim, J.-M. Campagne, D. Joseph, B. Andrioletti, Tetrahedron, 58, 2041 (2002);
7. (a) S. Bhaduri, "Homogeneous Catalysis: Mechanisms and Industrial Applications", Wiley-Interscience, New York, 2000;
8. (b) "Handbook of Organopalladium Chemistry for Organic Synthesis" ed. by E. Negishi, John Wiley and Sons, New York, 2002;
9. (c) "Comprehensive Organometallic Chemistry II" eds. by E. W. Abel, F. G. A. Stone, G. Wilkinson, Pergamon Press, New York, 1995;
10. (d) J. Tsuji, "Transition Metal Reagents and Catalysts", Wiley, Bath, England, 2000, pp 56-76;
11. (e) M. Beller, C. Bolm, " Transition Metals for Organic Chemistry", Wiley-VCH, Weinheim, Germany, 1, 158 (1998);
12. (f) G. Poli, G. Giambastiani, A. Heumann, Tetrahedron, 56, 5959 (2000);
13. (g) "Cross-Coupling Reactions: A Practical Guide" ed. by N. Miyaura, Topics in Current Chemistry Series 219, Springer, New York, 2002
14. (a) T. Hiyama, E. Shirakawa, Top. Curr. Chem., 219, 61 (2002);
15. (b) K. A. Horn, Chem. Rev., 95, 1317 (1995);
16. (c) Y. Hatanaka, T. Hiyama, Synlett, 1991,845
17. (a) M. Shimizu, K. Mochida, T. Hiyama, Angew. Chem. Int. Ed., 47, 9760 (2008);
18. (b) Y. You, C-G. An, J.-J. Kim, S. Y. Park, J. Org. Chem., 72, 6241 (2007);
19. (c) X.-M. Liu, C. He, J. Haung, J. Xu, Chem. Mater., 17, 434 (2005);
20. (d) S. Yamaguchi, C. Xu, H. Yamada, A. Wakamiya, J. Organomet. Chem., 690, 5365 (2005);
21. (a) W. Bains, R. Tacke, Curr. Opin. Drug Dis. Dev., 6, 526 (2003);
22. (b) G. A. Showwell, J. S. Mills, Drug Discov. Today, 8, 551 (2003);
23. (c) J. O. Daiss, C. Burschka, J. S. Mills, J. G. Montana, G. A. Showell, I. Fleming, C. Gaudon, D. Ivanova, H. Gronemeyer, R. Tacke, Organometallics, 24, 3192 (2005)
24. (a) "The Chemistry of Organic Silicon Compounds" eds. by S. Patai, Z. Rappoport, Wiley & Sons, New York, 2000;
25. (b) E.W. Colvin, "Silicon Reagents in Organic Synthesis", Academic Press, London, 1988
26. (a) Y. Hatanaka, T. Hiyama, Tetrahedron Lett., 28, 4715 (1987);
27. (b) K. Yamamoto, S. Suzuki, J. Tsuji, ibid., 21, 1653 (1980);
28. (c) H. Matsumoto, M. Kasahara, M. Takahashi, T. Arai, T. Nakao, Y. Nagai, J. Organomet. Chem., 250, 99 (1983);
29. (d) C. Eaborn, R. W. Griffiths, A. Pidcock, ibid., 225, 331 (1982);
30. (e) S. E. Denmark, J. M. Kallemeyn, Org. Lett., 5, 3483 (2003);
31. (f) E. McNeill, T. E. Barder, S. L. Buchwald, ibid., 9, 3785 (2007);
32. (g) E. Shirakawa, T. Kurahashi, H. Yoshida, T. Hiyama, Chem. Commun., 2000, 1895;
33. (h) L. J. Goosen, A.-R. S. Ferwanah, Synlett, 2000, 1801;
34. (i) M. Tobisu, Y. Kita, N. Chatani, J. Am. Chem. Soc, 128, 8152 (2006);
35. (j) H. Matsumoto, S. Nagashima, K. Yoshihiro, Y. Nagai, J. Organomet. Chem., 85, C1 (1975);
36. (k) D. Azarian, S. S. Dua, C. Eaborn, D. R. M. Walton, ibid., 117, C 55 (1976);
37. l) H. Matsumoto, K. Yoshihiro, S. Nagashima, H. Watanabe, Y. Nagai, ibid., 128,409 (1977)
38. (a) B. M. Trost, Science, 254, 1471 (1991);
39. (b) idem, Angew. Chem. Int. Ed., 34, 259 (1995)
40. F. A. Cotton, G. Wilkinson, C. A. Murillo, M. Bochmann, "Advanced Inorganic Chemistry, 5th ed", Wiley, New York, 1999
41. R. Boukherroub, C. Chatgilialoglu, G. Manuel, Organometallics, 15,1508(1996)
42. A. Kunai, T. Sakurai, E. Toyoda, M. Ishikawa, Y. Yamamoto, Organometallics, 13, 3233 (1994)
43. M. A. Esteruelas, J. Herrero, F. M. Lopez, M. Martin, L. A. Oro, Organometallics, 18,1110(1999)
44. (a) H. Fuwa, M. Sasaki, Org. Bio. Chem., 5, 1849 (2007);
45. (b) idem, Heterocycles, 76, 521 (2008)
46. J. Yang, M. Brookhart, J. Am. Chem. Soc, 129,12656 (2007)
47. M. Murata, K. Suzuki, S. Watanabe, Y. Masuda, J. Org. Chem., 62,8569 (1997)
48. (a) M. Murata, H. Yamasaki, T. Ueta, M. Nagata, M. Ishikura, S. Watanabe, Y. Masuda, Tetrahedron, 63, 4087 (2007);
49. (b) M. Murata, M. Ishikura, M. Nagata, S. Watanabe, Y. Masuda, Org. Lett., 4,1843 (2002)
50. M. Murata, H. Yamasaki, K. Uogoshi, S. Watanabe, Y. Masuda, Synthesis, 2007, 2944
51. M. Murata, K. Ota, H. Yamasaki, S. Watanabe, Y. Masuda, Synlett, 2007,1387
52. A. S. Manoso, P. DeShong, J. Org. Chem., 66, 7499 (2001)
53. (a) K. Komuro, K. Ishizaki, H. Suzuki, J. Org. Chem 86, 24 (2003);
54. (a) M. Murata, S. Watanabe, Y. Masuda, Tetrahedron Lett., 40, 9255 (1999);
55. (b) A. Ochida, S. Ito, T. Miyahara, H. Ito, M. Sawamura, Chem. Lett., 2006,294
56. Y. Yamanoi, J. Org. Chem., 70, 9607 (2005)
57. M. Murata, H. Ohara, R. Oiwa, S. Watanabe, Y. Masuda, Synthesis, 2006, 1771
58. A. Hamze, O. Provot, M. Alami, J.-D. Brion, Org. Lett., 8, 931 (2006)
59. M. Iizuka, Y. Kondo, Eur. J. Org. Chem., 2008,1161
60. (a) W. Gu, S. Liu, R. B. Silverman, Org. Lett., 4, 4171 (2002);
61. (b) S. Liu, W. Gu, D. Lo, X. Ding, M. Ujiki, T. E. Adrian, G. A. Soff, R. B. Silverman, J. Med. Chem., 48, 3630 (2005)
62. Y. Yamanoi, H. Nishihara, J. Org. Chem., 73, 6671 (2008)
63. Tilley D. Karshtedt, A. T. Bell, T. D. Tilley, Organometallics, 25,4471 (2006)
64. (a) T. Yamakawa, H. Kagechika, E. Kawachi, Y. Hashimoto, K. Shudo, J. Med. Chem., 33, 1430 (1990);
65. (b) N. A. Rizvi, J. L. Marshall, E. Ness, M. J. Hawkins, C. Kessler, H. Jacobs, W. D. Brenckman, Jr., J. S. Lee, W. Petros, W. K. Hong, J. M. Kurie, J. Clin. Oncol., 20, 3522 (2002);
66. (c) H. Kagechika, K. Shudo, J. Med. Chem., 48, 5875 (2005)
67. Y. Yamanoi, T. Taira, J.-I. Sato, I. Nakamula, H. Nishihara, Org. Lett., 9,4543 (2007)
68. F. Kakiuchi, N. Chatani, Adv. Synth. Cotal., 345, 1077 (2003)
69. B. Lu, J. R. Falck, Angew. Chem. Int. Ed., 47, 7508 (2008)
70. N. Tsukada, J. F. Hartwig, J. Am. Chem. Soc, 127, 5022 (2005)
71. H. Gilman, E. A. Zuech, J. Am. Chem. Soc, 81, 5925 (1959)
72. N. Rot, T. Nijbacker, R. Kreon, F. J. J. de Kanter, F. Bickelhaupt, M. Lutz, A. L. Spek, Organometallics, 19,1319 (2000)
73. (a) W.-S. Jin, Y. Makioka, T. Kitamura, Y. Fujiwara, Chem. Commun., 1999, 955;
74. (b) Y. Makioka, Y. Fujiwara, T. Kitamura, J. Organomet. Chem., 611, 509 (2000)