Iridium-catalyzed ortho -selective C-H silylation of aromatic compounds directed toward the synthesis of π-conjugated molecules with Lewis acid-base interaction

Organic Letters

Volumn 17, Issue 7, 2015, Pages 1758-1761

  Wakaki, Takayuki ^a   Kanai, Motomu ^a,b   Kuninobu, Yoichiro ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBON; IRIDIUM; LEWIS ACID; LEWIS BASE; SILICON;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND;

CATALYSIS; HYDROCARBONS, AROMATIC; HYDROGEN BONDING; IRIDIUM; LEWIS ACIDS; LEWIS BASES; MOLECULAR STRUCTURE; SILICON;

EID: 84926469470     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b00529     Document Type: Article

References (42)

1. Tokoro, Y.; Yeo, H.; Tanaka, K.; Chujo, Y. Chem. Commun. 2012, 48, 8541
2. Tokoro, Y.; Tanaka, K.; Chujo, Y. Org. Lett. 2013, 15, 2366
3. Xiao, Q.; Meng, X.; Kanai, M.; Kuninobu, Y. Angew. Chem., Int. Ed. 2014, 53, 3168
4. Kano, N.; Komatsu, F.; Kawashima, T. J. Am. Chem. Soc. 2001, 123, 10778
5. Kano, N.; Yamamura, M.; Kawashima, T. J. Am. Chem. Soc. 2004, 126, 6250
6. Kano, N.; Komatsu, F.; Yamamura, M.; Kawashima, T. J. Am. Chem. Soc. 2006, 128, 7097
7. Wakamiya, A.; Taniguchi, T.; Yamaguchi, S. Angew. Chem., Int. Ed. 2006, 45, 3170
8. Bosdet, M. J. D.; Piers, W. E.; Sorensen, T. S.; Parvez, M. Angew. Chem., Int. Ed. 2007, 46, 4940
9. Jaska, C. A.; Piers, W. E.; McDonald, R.; Parvez, M. J. Org. Chem. 2007, 72, 5234
10. Ishida, N.; Narumi, M.; Murakami, M. Org. Lett. 2008, 10, 1279
11. Ishida, N.; Moriya, T.; Goya, T.; Murakami, M. J. Org. Chem. 2010, 75, 8709
12. Ishida, N.; Narumi, M.; Murakami, M. Helv. Chim. Acta 2012, 95, 2474
13. Kuninobu, Y.; Iwanaga, T.; Omura, T.; Takai, K. Angew. Chem., Int. Ed. 2013, 52, 4431
14. Kano, N.; Yoshino, J.; Kawashima, T. Org. Lett. 2005, 7, 3909
15. Yoshino, J.; Kano, N.; Kawashima, T. Chem. Commun. 2007, 559
16. Yoshino, J.; Kano, N.; Kawashima, T. Tetrahedron 2008, 64, 7774
17. Yoshino, J.; Furuta, A.; Kambe, T.; Itoi, H.; Kano, N.; Kawashima, T.; Ito, Y.; Asashima, M. Chem.-Eur. J. 2010, 16, 5026
18. Kano, N.; Furuta, A.; Kambe, T.; Yoshino, J.; Shibata, Y.; Kawashima, T.; Mizorogi, N.; Nagase, S. Eur. J. Inorg. Chem. 2012, 1584
19. Yoshino, J.; Kano, N.; Kawashima, T. Dalton Trans. 2013, 42, 15826
20. Sakakura, T.; Tokunaga, Y.; Sodeyama, T.; Tanaka, M. Chem. Lett. 1987, 2375
21. Uchimaru, Y.; El Sayed, A. M. M.; Tanaka, M. Organometallics 1993, 12, 2065
22. Tsukada, N.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 5022
23. Williams, N. A.; Uchimaru, Y.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1995, 1129
24. Kakiuchi, F.; Igi, K.; Matsumoto, M.; Chatani, N.; Murai, S. Chem. Lett. 2001, 422
25. Kakiuchi, F.; Igi, K.; Matsumoto, M.; Hayamizu, T.; Chatani, N.; Murai, S. Chem. Lett. 2002, 396
26. Kakiuchi, F.; Matsumoto, M.; Tsuchiya, K.; Igi, K.; Hayamizu, T.; Chatani, N.; Murai, S. J. Organomet. Chem. 2003, 686, 134
27. Tobisu, M.; Ano, Y.; Chatani, N. Chem.-Asian J. 2008, 3, 1585
28. Ihara, H.; Suginome, M. J. Am. Chem. Soc. 2009, 131, 7502
29. Kanyiva, K. S.; Kuninobu, Y.; Kanai, M. Org. Lett. 2014, 16, 1968
30. Ishiyama, T.; Sato, K.; Nishio, Y.; Miyaura, N. Angew. Chem., Int. Ed. 2003, 42, 5346
31. Saiki, T.; Nishio, Y.; Ishiyama, T.; Miyaura, N. Organometallics 2006, 25, 6068
32. Murata, M.; Fukuyama, N.; Wada, J.-i.; Watanabe, S.; Masuda, Y. Chem. Lett. 2007, 910
33. Cheng, C.; Hartwig, J. F. Science 2014, 343, 853
34. Ureshino, T.; Yoshida, T.; Kuninobu, Y.; Takai, K. J. Am. Chem. Soc. 2010, 132, 14324
35. Simmons, E. M.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 17092
36. Kuninobu, Y.; Yamauchi, K.; Tamura, N.; Seiki, T.; Takai, K. Angew. Chem., Int. Ed. 2013, 52, 1520
37. Siegel, S.; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2456
38. Gao, D.-W.; Shi, Y.-C.; Gu, Q.; Zhao, Z.-L.; You, S.-L. J. Am. Chem. Soc. 2013, 135, 86
39. Deng, R.; Huang, Y.; Ma, X.; Li, G.; Zhu, R.; Wang, B.; Kang, Y.-B.; Gu, Z. J. Am. Chem. Soc. 2014, 136, 4472
40. Gao, D.-W.; Yin, Q.; Gu, Q.; You, S.-L. J. Am. Chem. Soc. 2014, 136, 4841
41. Liu, L.; Zhang, A.-A.; Zhao, R.-J.; Li, F.; Meng, T.-J.; Ishida, N.; Murakami, M.; Zhao, W.-X. Org. Lett. 2014, 16, 5336
42. Shibata, T.; Shizuno, T. Angew. Chem., Int. Ed. 2014, 53, 5410