Rhodium-catalyzed tandem cyclization/Si-C activation reaction for the synthesis of siloles

Angewandte Chemie - International Edition

Volumn 53, Issue 22, 2014, Pages 5667-5671

  Zhang, Qing Wei ^a   An, Kun ^a   He, Wei ^a  

^a Tsinghua University   (China)

Author keywords

heterocycles; luminescence; rhodium; silicon; synthetic methods

Indexed keywords

LUMINESCENCE; RHODIUM; SILICON;

HETEROCYCLES; PHOTOLUMINESCENT MATERIALS; RHODIUM CATALYSTS; RHODIUM-CATALYZED; SELECTIVE ACTIVATION; SYNTHETIC METHODS; SYNTHETIC STRATEGIES; TANDEM CYCLIZATION;

CHEMICAL ACTIVATION;

CARBON; HETEROCYCLIC COMPOUND; RHODIUM; SILANE DERIVATIVE; SILICON; SILOLE;

CATALYSIS; CHEMISTRY; CYCLIZATION; QUANTUM THEORY; SYNTHESIS;

CARBON; CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS; QUANTUM THEORY; RHODIUM; SILANES; SILICON;

EID: 84901607606     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201400828     Document Type: Article

References (64)

1. S. Yamaguchi, K. Tamao, Silicon-containing Polymers: The Science and Technology of their Synthesis and Applications (Eds.:, R. G. Jones, W. Ando, J. Chojnowski,), Kluwer Academic Publishers, Dordrecht, 2000, pp. 461-498
2. J. Y. Corey, in Advances in Organometallic Chemistry, Vol. 59 (Eds.:, F. H. Anthony, J. F. Mark,), Academic Press, New York, 2011, pp. 1-328.
3. M. Shimizu, K. Mochida, T. Hiyama, J. Phys. Chem. C 2011, 115, 11265
4. M. Shimizu, K. Mochida, M. Katoh, T. Hiyama, J. Phys. Chem. C 2010, 114, 10004
5. K. Geramita, J. McBee, Y. Shen, N. Radu, T. D. Tilley, Chem. Mater. 2006, 18, 3261
6. E. Pusztai, I. S. Toulokhonova, N. Temple, H. Albright, U. I. Zakai, S. Guo, I. A. Guzei, R. Hu, R. West, Organometallics 2013, 32, 2529
7. J. Liu, Y. Zhong, J. W. Y. Lam, P. Lu, Y. Hong, Y. Yu, Y. Yue, M. Faisal, H. H. Y. Sung, I. D. Williams, K. S. Wong, B. Z. Tang, Macromolecules 2010, 43, 4921.
8. S. J. Toal, K. A. Jones, D. Magde, W. C. Trogler, J. Am. Chem. Soc. 2005, 127, 11661
9. S. J. Toal, D. Magde, W. C. Trogler, Chem. Commun. 2005, 5465.
10. G. Lu, H. Usta, C. Risko, L. Wang, A. Facchetti, M. A. Ratner, T. J. Marks, J. Am. Chem. Soc. 2008, 130, 7670.
11. J. Chen, Y. Cao, Macromol. Rapid Commun. 2007, 28, 1714
12. R. C. Coffin, J. Peet, J. Rogers, G. C. Bazan, Nat. Chem. 2009, 1, 657
13. J. Hou, H. Y. Chen, S. Zhang, G. Li, Y. Yang, J. Am. Chem. Soc. 2008, 130, 16144
14. T. Y. Chu, J. Lu, S. Beaupre, Y. Zhang, J. R. Pouliot, S. Wakim, J. Zhou, M. Leclerc, Z. Li, J. Ding, Y. Tao, J. Am. Chem. Soc. 2011, 133, 4250.
15. X. Zhan, S. Barlow, S. R. Marder, Chem. Commun. 2009, 1948
16. S. Yamaguchi, T. Goto, K. Tamao, Angew. Chem. 2000, 112, 1761
17. Angew. Chem. Int. Ed. 2000, 39, 1695
18. K. Tamao, S. Yamaguchi, M. Shiro, J. Am. Chem. Soc. 1994, 116, 11715.
19. W. Rauf, J. M. Brown, Angew. Chem. 2008, 120, 4296
20. Angew. Chem. Int. Ed. 2008, 47, 4228
21. Y. Nakao, M. Takeda, T. Matsumoto, T. Hiyama, Angew. Chem. 2010, 122, 4549
22. Angew. Chem. Int. Ed. 2010, 49, 4447
23. M. Shindo, K. Matsumoto, K. Shishido, Angew. Chem. 2004, 116, 106
24. Angew. Chem. Int. Ed. 2004, 43, 104.
25. M. Shimizu, K. Mochida, T. Hiyama, Angew. Chem. 2008, 120, 9906
26. Angew. Chem. Int. Ed. 2008, 47, 9760
27. K. Mochida, M. Shimizu, T. Hiyama, J. Am. Chem. Soc. 2009, 131, 8350
28. R. Shintani, H. Otomo, K. Ota, T. Hayashi, J. Am. Chem. Soc. 2012, 134, 7305.
29. T. Ureshino, T. Yoshida, Y. Kuninobu, K. Takai, J. Am. Chem. Soc. 2010, 132, 14324
30. Y. Kuninobu, K. Yamauchi, N. Tamura, T. Seiki, K. Takai, Angew. Chem. 2013, 125, 1560
31. Angew. Chem. Int. Ed. 2013, 52, 1520.
32. T. Matsuda, Y. Suda, Y. Fujisaki, Synlett 2011, 813
33. T. Ohmura, K. Masuda, M. Suginome, J. Am. Chem. Soc. 2008, 130, 1526
34. T. Matsuda, Y. Ichioka, Org. Biomol. Chem. 2012, 10, 3175.
35. I. Ojima, D. A. Fracchiolla, R. J. Donovan, P. Banerji, J. Org. Chem. 1994, 59, 7594
36. M. Tobisu, M. Onoe, Y. Kita, N. Chatani, J. Am. Chem. Soc. 2009, 131, 7506
37. M. Onoe, K. Baba, Y. Kim, Y. Kita, M. Tobisu, N. Chatani, J. Am. Chem. Soc. 2012, 134, 19477
38. M. Yu, X. Fu, J. Am. Chem. Soc. 2011, 133, 15926.
39. Y. Liang, W. Geng, J. Wei, Z. Xi, Angew. Chem. 2012, 124, 1970
40. Angew. Chem. Int. Ed. 2012, 51, 1934
41. Y. Liang, S. Zhang, Z. Xi, J. Am. Chem. Soc. 2011, 133, 9204
42. T. Meng, K. Ouyang, Z. Xi, RSC Adv. 2013, 3, 14273.
43. T. Matsuda, S. Kadowaki, T. Goya, M. Murakami, Org. Lett. 2007, 9, 133
44. K. Ikenaga, K. Hiramatsu, N. Nasaka, S. Matsumoto, J. Org. Chem. 1993, 58, 5045
45. Y. Yabusaki, N. Ohshima, H. Kondo, T. Kusamoto, Y. Yamanoi, H. Nishihara, Chem. Eur. J. 2010, 16, 5581
46. W. S. Palmer, K. A. Woerpel, Organometallics 1997, 16, 1097
47. T. Matsuda, S. Kadowaki, M. Murakami, Chemm. Commun. 2007, 2627
48. T. Matsuda, Y. Yamaguchi, M. Shigeno, S. Sato, M. Murakami, Chem. Commun. 2011, 47, 8697.
49. I. Fleming, A. Barbero, D. Walter, Chem. Rev. 1997, 97, 2063, and references therein.
50. N. Isono, M. Lautens, Org. Lett. 2009, 11, 1329
51. D. Shu, W. Song, X. Li, W. Tang, Angew. Chem. 2013, 125, 3319
52. Angew. Chem. Int. Ed. 2013, 52, 3237
53. X. Li, W. Song, W. Tang, J. Am. Chem. Soc. 2013, 135, 16797.
54. T. E. Müller, K. C. Hultzsch, M. Yus, F. Foubelo, M. Tada, Chem. Rev. 2008, 108, 3795.
55. C. M. So, S. Kume, T. Hayashi, J. Am. Chem. Soc. 2013, 135, 10990.
56. T. Seiser, N. Cramer, Angew. Chem. 2010, 122, 10361
57. Angew. Chem. Int. Ed. 2010, 49, 10163.
58. P. J. Davidson, M. F. Lappert, R. Pearce, Acc. Chem. Res. 1974, 7, 209.
59. K. Ouyang, Z. Xi, Acta Chim. Sin. 2013, 71, 13.
60. CCDC 948123 (2g) and 979513 (3b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif. (Also see SI)
61. X.-K. Chen, L.-Y. Zou, A.-M. Ren, J.-X. Fan, Phys. Chem. Chem. Phys. 2011, 13, 19490.
62. Y. Yamanoi, H. Nishihara, J. Org. Chem. 2008, 73, 6671.
63. T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685.
64. Z. Yu, Y. Lan, J. Org. Chem. 2013, 78, 11501.