General and practical one-pot synthesis of dihydrobenzosiloles from styrenes

Organic Letters

Volumn 14, Issue 3, 2012, Pages 914-917

  Kuznetsov, Alexey ^a   Gevorgyan, Vladimir ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; STYRENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; HYDROGENATION; SYNTHESIS;

BENZENE; CATALYSIS; CYCLIZATION; HYDROGENATION; MOLECULAR STRUCTURE; STYRENES;

EID: 84856728404     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol203428c     Document Type: Article

References (26)

1. Tsukada, N.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 5022
2. Lu, B.; Falck, J. R. Angew. Chem., Int. Ed. 2008, 47, 7508
3. Ureshino, T.; Yoshida, T.; Kuninobu, Y.; Takai, K. J. Am. Chem. Soc. 2010, 132, 14324
4. Simmons, E. M.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 17092
5. Furukawa, S.; Kobayashi, J.; Kawashima, T. J. Am. Chem. Soc. 2009, 131, 14192
6. For an example of hydrogenation of dihydrobenzosilole, see: Benkeser, R. A.; Mozdzen, E. C.; Muench, W. C.; Roche, R. T.; Siklosi, M. P. J. Org. Chem. 1979, 44, 1370
7. Belzner, J.; Dehnert, U.; Ihmels, H. Tetrahedron 2001, 57, 511
8. Ando, W.; Sekiguchi, A. J. Org. Chem. 1980, 45, 5286. See also refs 1 and 6
9. Corma, A.; Gonzalez-Arellano, C.; Iglesias, M.; Sanchez, F. Angew. Chem., Int. Ed. 2007, 46, 7820
10. Debono, N.; Iglesias, M.; Sanchez, F. Adv. Synth. Catal. 2007, 349, 2470
11. Takahashi, T. J. Am. Chem. Soc. 1991, 113, 8564
12. 2, see: Takaki, K.; Sonoda, K.; Kousaka, T.; Koshoji, G.; Shishido, T.; Takehira, K. Tetrahedron Lett. 2001, 42, 9211
13. Nielsen, L.; Skrydstrup, T. J. Am. Chem. Soc. 2008, 130, 113145
14. Betley, T. A.; Peters, J. C. Angew. Chem., Int. Ed. 2003, 42, 2385
15. Belyakova, Z. V.; Pomerantseva, M. G.; Efimova, L. A.; Chernyshev, E. A.; Storozhenko, P. A. Rus. J. Gen. Chem. 2010, 80, 728
16. Gareau, D.; Sui-Seng, C.; Groux, L. F.; Brisse, F.; Zargarian, D. Organometallics 2005, 24, 4003
17. Yamamoto, K.; Hayashi, T.; Uramoto, Y.; Ito, R.; Kumada, M. J. Organomet. Chem. 1976, 118, 331
18. Rodenberg, L.; Davis, C. W.; Yao J. Am. Chem. Soc. 2001, 123, 5120
19. Chang, L. S.; Corey, J. Y. Organometallics 1989, 8, 1885
20. 3-catalyzed hydrosilylation of alkenes, see: Rubin, M.; Schwier, T.; Gevorgyan, V. J. Org. Chem. 2002, 67, 1936
21. Livendahl, M.; Echavarren, A. M. Isr. J. Chem. 2010, 50, 630
22. Wei, Y.; Kan, J.; Wang, M.; Su, W.; Hong, M. Org. Lett. 2009, 11, 3346
23. For a very recent study on the CMD-type mechanism in the Ir-catalyzed C - H arylation, see: Garcia-Melchor, M.; Gorelsky, S. I.; Woo, T. K. Chem. - Eur. J. 2011, 17, 13847
24. Wong, W. W. H.; Hooper, J. F.; Holmes, A. B. Aust. J. Chem. 2009, 62, 393
25. Wong, W. W. H.; Holmes, A. B. Adv. Polym. Sci. 2008, 212, 85
26. Tamao, K.; Uchida, M.; Izumizawa, T.; Furukawa, K.; Yamaguchi, S. J. Am. Chem. Soc. 1996, 118, 11974