Generation and reactions of o-bromophenyllithium without benzyne formation using a microreader

Journal of the American Chemical Society

Volumn 129, Issue 11, 2007, Pages 3046-3047

  Usutani, Hirotsugu ^a   Tomida, Yutaka ^a   Nagaki, Aiichiro ^a   Okamoto, Hideho ^a   Nokami, Toshiki ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 BROMOPHENYLLITHIUM; BROMINE; LITHIUM DERIVATIVE; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INDUSTRY; CHEMICAL REACTION; CHEMICAL STRUCTURE; MICROREACTOR; REACTION ANALYSIS; REACTOR; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 33947378268     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja068330s     Document Type: Article

References (38)

1. Reviews: For example (a) Fletcher, P. D. I.; Haswell, S. J.; Pombo-Villar, E.; Warrington, B. H.; Watts, P.; Wong, S. Y. F.; Zhang, X. Tetrahedron 2002, 58, 4735.
2. (b) Jähnisch, K.; Hesse], V.; Löwe, H.; Baerns; M. Angew. Chem., Int. Ed. 2004, 43; 406.
3. (c) Doku, G. N.; Verboom, W.; Reinhoudt, D. N.; van den Berg, A. Tetrahedron 2005, 61, 2733.
4. (d) Yoshida, J. Chem. Commun. 2005, 4509.
5. Recent examples: (a) de Bellefon, C.; Tanchoux, N.; Caravieilhes, S.; Grenouillet, P.; Hessel, V. Angew. Chem., Int. Ed. 2000, 39, 3442.
6. (b) Watts, P.; Wiles, C.; Haswell, S. J.; Pombo-Villar, E.; Styring, P. Chem. Commun. 2001, 990.
7. (c) Hisamoto, H.; Saito, T.; Tokeshi, M.; Hibara, A.; Kitamori, T. Chem. Commun. 2001, 2662.
8. (d) Suga, S.; Okajima, M.; Fujiwara, K.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 7941.
9. (e) Wiles, C.; Watts, P.; Haswell, S. J.; Pombo-Villar, E. Chem. Commun. 2002, 1034.
10. (f) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691.
11. (g) Ueno, M.; Hisamoto, H.; Kitamori, T.; Kobayashi, S. Chem. Commun. 2003, 936.
12. (h) Garcia-Egido, E.; Spikmans, V.; Wong, S. Y. F.; Warrington, B. H. Lab. Chip 2003, 3, 73.
13. (i) Lai, S. M.; Martin-Aranda, R.; Yeung, K. L. Chem. Commun. 2003, 218.
14. (j) Mikami, K.; Yamanaka, M.; Islam, M. N.; Kudo, K.; Seino, N.; Shinoda, M. Tetrahedron Lett. 2003, 44, 7545.
15. (k) Kobayashi, J.; Mori, Y.; Okamoto, K.; Akiyama, R.; Ueno, M.; Kitamori, T.; Kobayashi, S. Science 2004, 304, 1305.
16. (l) Wu, T.; Mei, Y.; Cabral, J. T.; Xu, C.; Beers, K. L. J. Am. Chem. Soc. 2004, 126, 9880.
17. (m) Horcajada, R.; Okajima, M.; Suga, S.; Yoshida, J. Chem. Commun. 2005, 1303.
18. (n) Ducry, L.; Roberge, D. M. Angew. Chem., Int. Ed. 2005, 44, 7972.
19. (o) Nagaki, A.; Togai, M.; Suga, S.; Aoki, N.; Mae, K.; Yoshida, J. J. Am. Chem. Soc. 2005, 127, 11666.
20. (p) Iwasaki, T.; Yoshida, J. Macromolecules 2005, 38, 1159.
21. (q) He, P.; Watts, P.; Marken, F.; Haswell, S. J. Angew. Chem., Int. Ed. 2006, 45, 4146.
22. (r) Midorikawa, K.; Suga, S.; Yoshida, J. Chem. Commun. 2006, 3794.
23. (a) Kawaguchi, T.; Miyata, H.; Ataka, K.; Mae, K.; Yoshida, J. Angew. Chem., Int. Ed. 2005, 44, 2413.
24. (b) Nagaki, A.; Kawamura, K.; Suga, S.; Ando, T.; Sawamoto, M.; Yoshida, J. J. Am. Chem. Soc. 2004, 126, 14702.
25. (a) Gilman, H.; Gorsich, R. D. J. Am. Chem. Soc. 1956, 78, 2217.
26. (b) Chen, L. S.; Chen, G. J.; Tamborski, C. J. Organometal. Chem. 1980, 193, 283.
27. (c) Prabhu, U. D. G.; Eapen, K. C.; Tamborski, C. J. Org. Chem. 1984, 49, 2792.
28. (d) Leroux, F.; Schlosser, M. Angew. Chem., Int. Ed. 2002, 41, 4272.
29. See also: (e) Luliski, S.; Serwatowski, J. J. Org. Chem. 2003, 68, 5384.
30. o-Bromophenylmagnesium reagents, which are more stable than the corresponding lithium reagent, have been reported in the literature: (a) Ghosh, T. Hart, H. J. Org. Chem. 1988, 53, 3555.
31. (b) Boymond, L.; Rottländer, M.; Chiez, G.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 1701.
32. (c) Inoue, A.; Kitagawa, K.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2001, 66, 4333.
33. (d) Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 3333.
34. Halogen-lithium exchange reactions of simple aromatic halides in micro systems: (a) Schwalbe, T.; Autze, V.; Hohmann, M.; Stirner, W. Org. Process Res. Dev. 2004, 8, 440.
35. (b) Zhang, X.; Stefanick, S.; Villani, F. J. Org. Process Res. Dev. 2004, 8, 455.
36. Although it is difficult to determine the mixing time for the T-shape mixers, it seems to be much less than 0.8 sec at the present flow rate, because most of the starting material (o-dibromobenzene) was consumed within this residence time.
37. Residence time was controlled by changing the length of R1 with the fixed flow rate.
38. Microtube reactors made by stainless steel are quite effective for rapid heat transfer. Thermal decomposition of a radical initiator revealed that the temperature inside the microtube reactor is practically the same as the bath temperature even if highly exothermic radical polymerization takes place in the microtube reactor. See, Iwasaki, T.; Yoshida, J. Macromolecules 2005, 38, 1159.