Transition metal-catalyzed silylation of organic halides with hydrosilanes

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 68, Issue 8, 2010, Pages 845-853

  Murata, Miki ^a   Masuda, Yuzuru ^a  

^a KITAMI INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Aromatic hydrocarbons; Aryl halides; Arylsilanes; Cross coupling reaction; Hydrosilanes; Silylation; Transition metal catalysts

Indexed keywords

ARYL HALIDES; ARYLSILANES; CROSS COUPLING REACTIONS; HYDROSILANES; SILYLATIONS; TRANSITION METAL CATALYSTS;

AROMATIZATION; CATALYSIS; CATALYSTS; METAL HALIDES; ORGANIC COMPOUNDS; PALLADIUM; PALLADIUM COMPOUNDS; PLATINUM; RHODIUM; RHODIUM COMPOUNDS; SILANES; TRANSITION METALS;

AROMATIC HYDROCARBONS;

EID: 77957842840     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.68.845     Document Type: Article

References (90)

1. (a) "Metal-Catalyzed Cross-Coupling Reactions" eds. by F. Diederich, P. J. Stang, Wiley-VCH, New York, 1998;
2. (b) "Cross-Coupling Reactions: A Practical Guide" ed. by N. Miyaura, Springer-Verlag. New York, 2002;
3. (c) "Metal-Catalyzed Cross-Coupling Reactions, 2nd ed" eds. by A. de Meijere, F. Diederich, Wiley-VCH, Weinheim, 2004
4. (a) T. Hiyama Y. Hatanaka Pure Appl. Chem., 66, 1471(1994);
5. (b) T. Hiyama, J. Organomet Chem., 653, 58(2002);
6. (c) S. E. Denmark, R F. Sweis, Acc. Chem. Res., 35. 835(2002);
7. (d) T. Hiyama, E. Shirakawa, Top. Curr. Chem., 219. 61(2002);
8. (e) A. K. Sahoo, T. Oda, Y. Nakao, T. Hiyama, Adv. Synth. Catal., 346, 1715(2004);
9. (f) S. E. Denmark, J. D. Baird, Chem. Eur. J., 12, 4954(2006);
10. (g) Y. Nakao, A. K. Sahoo, H. Imanaka, A. Yada, T. Hiyama, Pure Appl. Chem., 78. 435(2006)
11. (a) E. W. Colvin, "Silicon Reagents in Organic Synthesis", Academic Press, Londoa 1988;
12. (b) The Chemistry of Organic Silicon Compounds" eds. by S. Patai, Z. Rappoport, John Wiley & Sons, Chichester, 1989
13. (a) H. Matsumoto, S. Nagashima, K. Yoshihiro, Y. Nagai, J. Organomet. Chem., 85, C1 (1975);
14. (b) D. Azariaa, S. S. Dua, C. Eaborn, D. R. M. Walton, J. Organomet. Chem., 117, C55 (1976);
15. (c) H. Matsumoto, K. Yoshihiro, S. Nagashima, H. Watanabe, Y. Nagai, J. Organomet. Chem., 128, 409(1977);
16. (d) H. Matsumoto, K. Shono, Y. Nagai. J. Organomet. Chem., 208, 145(1981);
17. (e) C. Eaborn, R. W. Griffiths, A. Pidcock. J. Organomet. Chem., 225, 331(1982);
18. (f) H. Matsumoto, M. Kasahara, I. Matsubara, M. Takahashi, T. Arai, M. Hasegawa, T. Nakano, Y. Nagai, J. Organomet. Chem., 250. 99(1983);
19. (g) H. Urata, H. Suzuki, Y. Moro-oka, T. Ikawa, Bull. Chem. Soc. Jpn., 57. 607(1984);
20. (h) Y. Hatanaka, T. Hiyama, Tetrahedron Lett., 28, 4715(1987);
21. (i) J. D. Rich. J. Am. Chem. Soc., 111. 5886(1989);
22. (j) T. E. Krafft, J. D. Rich, P. J. McDermott, J. Org. Chem., 55, 5430(1990);
23. (k) P. Babin, B. Bennetau, M. Theurig, J. Dunoguès, J. Organomet. Chem., 446, 135(1993);
24. (l) Y. Tsuji, S. Kajita, S. Isobe, M. Funato, J. Org. Chem., 58, 3607(1993);
25. (m) Y. Tsuji, M. Funato, M. Ozawa, H. Ogiyama, S Kajita, T. Kawamura, J. Org. Chem., 61, 5779(1996);
26. (n) E. Shirakawa, T. Kurahashi, H. Yoshida, T. Hiyama, Chem. Commun., 2000, 1895;
27. (o) L. J. Goossen, A.-R. S. Ferwanah, Synlett. 2000, 1801;
28. (p) S. E. Denmark, J. M. Kallemeyn, Org. Lett., 5, 3483(2003);
29. (q) T. Iwasawa, T. Komano, A. Tajima, M. Tokunaga, Y. Obora, T. Fujihara, Y. Tsuji, Organometallics, 25, 4665(2006);
30. (r) E. McNeill, T. E. Barder, S. L. Buchwald, Org. Lett. 9, 3785(2007)
31. N. Furuya, T. Sukawa, J. Organomet. Chem., 96, C1 (1975)
32. S. Kobayashi. K. Nishio, J. Am. Chem. Soc., 117, 6392(1995)
33. (a) J. D. Citron. J. E. Lyons, L. H. Sommer, J. Org. Chem., 34, 638(1969);
34. (b) D. Seyferth, C. C. Prud'homme. W. L. Wang. J. Organomet. Chem., 277, 203(1984);
35. (c) A. Kunai, T. Sakurai, E. Toyoda, M. Ishikawa, Y. Yamamoto, Organometallics. 13, 3233 (1994);
36. (d) R. Boukherroub, C. Chatgilialoglu, G. Manuel, Organometallics., 15, 1508(1996)
37. M. A. Esteruelas, J. Herrero, F. M. López, M. Martin, L. A. Oro, Organometallics. 18, 1110(1999)
38. K. Ezbiansky, P. I. Djurovich, M. LaForest, D. J. Sinning, R. Zayes, D. H. Berry, Organometallics, 17, 1455(1998)
39. Y. Yamanoi, H. Nishihara, J. Synth. Org. Chem., Jpn., 67, 778 (2009)
40. (a) P. DeShong, C. J. Handy, M. E. Mowery, Pure Appl. Chem., 72, 1655(2000);
41. (b) M. Murata, R. Shimazaki, S. Watanabe, Y. Masuda, Synthesis, 2001, 2231;
42. (c) M. Murata, R. Shimazaki, M. Ishikura, S. Watanabe, Y. Masuda, Synthesis., 2002, 717;
43. (d) S. Oi, Y. Honma, Y. Inoue, Org. Lett., 4, 667(2002);
44. (e) S. E. Denmark, N. Amishiro, J. Org. Chem., 68, 6997(2003);
45. (f) T. Nishikata, Y. Yamamoto, N. Miyaura, Chem. Lett., 32, 752(2003);
46. (g) T. Koike, X. Du, T. Sanada, Y. Danda, A. Mori, Angew. Chem. Int. Ed.. 42, 89 (2003);
47. (h) S. Yang, B. Li, X. Wan, Z. Shi, J. Am. Chem. Soc., 129, 6066(2007);
48. D. Tomita, K. Yamatsugu, M. Kanai, M. Shibasaki, J. Am. Chem. Soc., 131, 6946(2009)
49. (a) K. J. Shea, D. A Loy, O. Webster, J. Am. Chem. Soc., 114, 6700(1992);
50. (b) H. J. Frohn, M. Giesea, A. Klose, A. Lewin, V. V. Bardin, J. Organomet. Chem., 506, 155(1996);
51. (c) R. J. P. Corriu, A. Mix, G. F. Lanneau, J. Organomet. Chem., 570, 183 (1998);
52. (d) J. P. Bezombes, C. Chuit, R. J. P. Corriu, C. Reye, J. Mater. Chem., 8, 1749(1998);
53. (e) A. S. Manoso, C. Ahn, A. Soheili, C. J. Handy, R. Correia, W. M. Seganish, P. DeShong, J. Org. Chem., 69, 8305(2004)
54. M. Murata, K. Suzuki, S. Watanabe, Y. Masuda, J. Org. Chem., 62, 8569(1997)
55. R. A. Benkeser, J. M. Gaul, W. E. Smith, J. Am. Chem. Soc., 91, 3666(1969)
56. A. S. Manoso, P. DeShong, J. Org. Chem., 66, 7449(2001)
57. (a) M. Murata, M. Ishikura, M. Nagata S. Watanabe, Y. Masuda Org. Lett., 4, 1843(2002);
58. (b) M. Murata, H. Yamasaki, T. Ueta, M. Nagata, M. Ishikura, S. Watanabe, Y. Masuda, Tetrahedron, 63, 4087(2007)
59. (a) Y. Maegawa, Y. Goto, S. Inagaki, T. Shimada, Tetrahedron Lett. 47, 6957(2006);
60. (b) T. P. Nguyen, P. Hesemann, P. Gaveau, J. J. E. Moreau, J. Mater. Chem., 19, 4164(2009)
61. M. Murata, H. Yamasaki, K. Uogishi, S. Watanabe, Y. Masuda, Synthesis, 2007, 2944
62. (a) S. Riggleman, P. DeShong, J. Org. Chem., 68, 8106(2003);
63. (b) J. W. Faller, R. G. Kultyshev, Organometallics. 21, 5911 (2002)
64. (a) D. Karshtedt, A. T. Bell, T. D. Tilley, Organometallics, 25, 4471(2006);
65. (b) Y. Yamanoi, H. Nishihara, J. Org. Chem., 73, 6671(2008)
66. Y. Nishihara, M. Takemura, K. Osakada, Organometallics, 21, 825(2002)
67. (a) M. Murata, S. Watanabe, Y. Masuda, Tetrahedron Lett., 40, 9255(1999);
68. R. J. P. Corriu, C. Guérin, "Encyclopedia of Reagents for Organic Synthesis" ed. by L. A. Paquette, John Wiley & Sons, New York, 1995, VoL 7. p 5083
69. M. Murata, K. Ota, H. Yamasaki, S. Watanabe, Y. Masuda, Synlett. 2007, 1387
70. A. Hamze, O. Provot, M. Alami, J. D. Brion, Org. Lett., 8, 931 (2006)
71. G. Berthon-Gelloz, J. M. Schumers, G. De Bo, I. E. Mark, J. Org. Chem., 73, 4190(2008)
72. W. A. Gustavson, P. S. Epstein, M. D. Curtis. Organometallics, 1, 884(1982)
73. (a) F. Kakiuchi, N. Chatani, Adv. Synth. Catal., 345, 1077 (2003);
74. (b) T. Ishiyama, J. Synth. Org. Chem., Jpn., 63, 440 (2005)
75. (a) T. Ishiyama, K. Sato, Y. Nishio, N. Miyaura, Angew. Chem. Int. Ed., 42, 5346(2003);
76. (b) T. Ishiyama, K. Sato, Y. Nishio, T. Saiki, N. Miyaura, Chem. Commun., 2005, 5065;
77. (c) T. Saiki, Y. Nishio, T. Ishiyama, N. Miyaura, Organometallics. 25, 6068 (2006)
78. M. Murata, N. Fukuyama, J.-I. Wada, S. Watanabe, Y. Masuda, Chem. Lett., 36, 910(2007)
79. N. Tsukada, J. F. Hartwig, J. Am. Chem. Soc., 127, 5022(2005)
80. (a) Y. Yamanoi, J. Org. Chem., 70, 9607(2005);
81. (b) Y. Yamanoi, H. Nishihara, Tetrahedron Lett., 47, 7157(2006)
82. M. Murata, H. Ohara, R. Oiwa, S. Watanabe, Y. Masuda, Synthesis, 2006, 1771
83. M. Iizuka, Y. Kondo, Eur. J. Org. Chem., 2008, 1161