Palladium-catalyzed synthesis of benzosilolo[2,3- b ]indoles via cleavage of a C(sp3)-Si bond and consequent intramolecular C(sp 2)-Si coupling

Journal of the American Chemical Society

Volumn 133, Issue 24, 2011, Pages 9204-9207

  Liang, Yun ^a,b   Zhang, Shaoguang ^a   Xi, Zhenfeng ^a,c  

^a PEKING UNIVERSITY   (China)

^b HUNAN NORMAL UNIVERSITY   (China)

^c SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC PROCESS; EFFICIENT PROCESS;

ALDEHYDES; CATALYSIS;

SILICON;

ALDEHYDE; BENZOSILOLO [2,3 BETA] INDOLE DERIVATIVE; INDOLE DERIVATIVE; PALLADIUM; SILICON; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; COUPLING FACTOR; SYNTHESIS;

CARBON; CATALYSIS; INDOLES; PALLADIUM; SILICON;

EID: 79959221584     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2024959     Document Type: Article

References (71)

1. For reviews, see: Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599
2. Franz, A. K.; Woerpel, K. A. Acc. Chem. Res. 2000, 33, 813
3. Rauf, W.; Hazari, A.; Gouverneur, V.; Brown, J. M. Pure Appl. Chem. 2010, 82, 1415
4. Hiyama, T. J. Synth. Org. Chem. Jpn. 2010, 68, 729
5. 2)-Si bonds, see: Hiyama, T. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
6. Hiyama, T. J. Organomet. Chem. 2002, 653, 58
7. Denmark, S. E.; Sweiss, R. F. Acc. Chem. Res. 2002, 35, 835
8. Spivey, A. C.; Gripton, C. J. G.; Hannah, J. P. Curr. Org. Synth. 2004, 1, 211
9. Denmmark, S. E.; Baird, J. D. Chem.-Eur. J. 2006, 12, 4954 For representative examples, see: Nakao, Y.; Imanaka, H.; Sahoo, A. K.; Yada, A.; Hiyama, T. J. Am. Chem. Soc. 2005, 127, 6952
10. Alacid, E.; Nájera, C. Adv. Synth. Catal. 2006, 348, 2085
11. Yang, S.; Li, B.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 6066
12. Dai, X.; Strotman, N. A.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 3302
13. Zhang, L.; Wu, J. J. Am. Chem. Soc. 2008, 130, 12250
14. For selected examples of transition-metal-catalyzed cleavage of C(sp)-Si bonds, see: Wu, M.-J.; Wei, L.-M.; Lin, C.-F.; Leou, S.-P.; Wei, L.-L. Tetrahedron 2001, 57, 7839
15. Sommer, W. J.; Weck, M. Adv. Synth. Catal. 2006, 348, 2101
16. Horita, A.; Tsurugi, H.; Satoh, T.; Miura, M. Org. Lett. 2008, 10, 1751
17. Huang, H.; Liu, H.; Jiang, H.; Chen, K. J. Org. Chem. 2008, 73, 6037
18. Sakai, N.; Komatsu, R.; Uchida, N.; Ikeda, R.; Konakahara, T. Org. Lett. 2010, 12, 1300
19. van Klink, G. P. M.; de Boer, H. J. R.; Schat, G.; Akkerman, O. S.; Bickelhaupt, F.; Spek, A. L. Organometallics 2002, 21, 2119
20. Wang, Z.; Fang, H.; Xi, Z. Tetrahedron Lett. 2005, 46, 499
21. Hudrlik, P. F.; Dai, D.; Hudrlik, A. M. J. Organomet. Chem. 2006, 691, 1257
22. Wang, C.; Luo, Q.; Sun, H.; Guo, X.; Xi, Z. J. Am. Chem. Soc. 2007, 129, 3094
23. Yu, N.; Wang, C.; Zhao, F.; Liu, L.; Zhang, W.-X.; Xi, Z. Chem.-Eur. J. 2008, 14, 5670
24. Palmer, W. S.; Woerpel, K. A. Organometallics 1997, 16, 4824
25. Franz, A. K.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 949
26. Cho, J. E.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679
27. Chu, L.; Qing, F.-L. Org. Lett. 2010, 12, 5060
28. Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2010, 132, 7262
29. Hosomi, A. Acc. Chem. Res. 1988, 21, 200
30. Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 37, 57
31. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063
32. Mateo, C.; Fernández-Rivas, C.; Echavarren, A. M.; Cárdenas, D. J. Organometallics 1997, 16, 1997
33. Matsuda, T.; Kadowaki, S.; Yamaguchi, Y.; Murakami, M. Chem. Commun. 2008, 2744
34. Rauf, W.; Brown, J. M. Angew. Chem., Int. Ed. 2008, 47, 4228
35. Tobisu, M.; Onoe, M.; Kita, Y.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 7506
36. Conjugated silole derivatives are of great importance as organic materials for electronic and optoelectronic devices. For reviews, see: Yamaguchi, S.; Tamao, K. Silicon-Containing Polymers: The Science and Technology of their Synthesis and Applications; Jones, R. G.; Ando, W.; Chojnowski, J., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2000; pp 461-498.
37. Yamaguchi, S.; Tamao, K. J. Organomet. Chem. 2002, 653, 223
38. Hissler, M.; Dyer, P. W.; Reau, R. Coord. Chem. Rev. 2003, 244, 1
39. Yamaguchi, S.; Xu, C.; Okamoto, T. Pure Appl. Chem. 2006, 78, 721
40. Chen, J.; Cao, Y. Macromol. Rapid Commun. 2007, 28, 1714
41. Liu, J.; Zhong, Y.; Lam, J. W. Y.; Lu, P.; Hong, Y.; Yu, Y.; Yue, Y.; Faisal, M.; Sung, H. H. Y.; Williams, I. D.; Wong, K. S.; Tang, B. Z. Macromolecules 2010, 43, 4921
42. The synthesis of benzosilolo[3,2- b ]indoles was reported, and benzosilolo[2,3- b ]indoles were mentioned as byproducts. See: Shimizu, M.; Mochida, K.; Hiyama, T. Angew. Chem., Int. Ed. 2008, 47, 9760
43. Mochida, K.; Shimizu, M.; Hiyama, T. J. Am. Chem. Soc. 2009, 131, 8350 For examples of other silicon-bridged polyheteroarenes, see: Usta, H.; Lu, G.; Facchetti, A.; Marks, T. J. J. Am. Chem. Soc. 2006, 128, 9034
44. Huo, L.; Chen, H.-Y.; Hou, J.; Chen, T. L.; Yang, Y. Chem. Commun. 2009, 5570
45. Masuda, K.; Ohmura, T.; Suginome, M. Organometallics 2011, 30, 1322
46. Xi, Z.; Liu, X.; Lu, J.; Bao, F.; Fan, H.; Li, Z.; Takahashi, T. J. Org. Chem. 2004, 69, 8547
47. Xi, Z.; Song, Z.; Liu, G.; Liu, X.; Takahashi, T. J. Org. Chem. 2006, 71, 3154
48. Zhang, H.-J.; Song, Z.; Wang, C.; Bruneau, C.; Xi, Z. Tetrahedron Lett. 2008, 49, 624
49. Wang, C.; Deng, L.; Yan, J.; Wang, H.; Luo, Q.; Zhang, W.-X.; Xi, Z. Chem. Commun 2009, 4414
50. Zhang, H.-J.; Wei, J.; Zhao, F.; Liang, Y.; Wang, Z.; Xi, Z. Chem. Commun. 2010, 46, 7439
51. Liang, Y.; Meng, T.; Zhang, H.-J.; Xi, Z. Synlett 2011, 911
52. Martín, R.; Larsen, C. H.; Cuenca, A.; Buchwald, S. L. Org. Lett. 2007, 9, 3379
53. Fletcher, A. J.; Bax, M. N.; Willis, M. C. Chem. Commun. 2007, 4764
54. Yuan, X.; Xu, X.; Zhou, X.; Yuan, J.; Mai, L.; Li, Y. J. Org. Chem. 2007, 72, 1510
55. Willis, M. C.; Brace, G. N.; Findlay, T. J. K.; Holmes, I. P. Adv. Synth. Catal. 2006, 348, 851
56. Willis, M. C.; Brace, G. N.; Holmes, I. P. Angew. Chem., Int. Ed. 2005, 44, 403
57. For Si-Pd bond formation, see: Takeyama, Y.; Nozaki, K.; Matsumoto, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 1461
58. Tanaka, Y.; Yamashita, H.; Tanaka, M. Organometallics 1996, 15, 1524
59. Palmer, W.; Woerpel, K. A. Organometallics 2001, 20, 3691
60. Tanabe, M.; Osakada, K. Chem.-Eur. J. 2004, 10, 416
61. Liu, J.; Sun, X.; Miyazaki, M.; Liu, L.; Wang, C.; Xi, Z. J. Org. Chem. 2007, 72, 3137
62. Fujiwara, S.; Toyofuku, M.; Kuniyasu, H.; Kambe, N. Pure Appl. Chem. 2010, 82, 565
63. Buchner, K. M.; Woerpel, K. A. Organometallics 2010, 29, 1661
64. Paluki, M.; Wolfe, P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395
65. Torraca, K. E.; Huang, X.; Parrish, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 10770
66. Han, X.-L.; Liu, G.-X.; Lu, X.-Y. Chin. J. Org. Chem. 2005, 25, 1182
67. Zask, A.; Helquist, P. J. Org. Chem. 1978, 43, 1619
68. Viciu, M. S.; Grasa, G. A.; Nolan, S. P. Organometallics 2001, 20, 3607
69. Navarro, O.; Kaur, H.; Mahjoor, P.; Nolan, S. P. J. Org. Chem. 2004, 69, 3173
70. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2002, 102, 4009
71. Moon, J.; Lee, S. J. Organomet. Chem. 2009, 694, 473