Meta halogenation of 1,3-disubstituted arenes via iridium-catalyzed arene borylation

Journal of the American Chemical Society

Volumn 129, Issue 50, 2007, Pages 15434-15435

  Murphy, Jaclyn M ^a   Liao, Xuebin ^a   Hartwig, John F ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

BORON DERIVATIVE; BROMIDE; CHLORIDE; COPPER DERIVATIVE; HALIDE; IRIDIUM; LIGAND; METAL COMPLEX; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; HALOGENATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 37849049915     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja076498n     Document Type: Article

References (29)

1. Smith, M. B.; March, J., March's Advanced Organic Chemistry, 5th ed.; John Wiley and Sons: New York, 2001.
2. Snieckus, V., Chem. Rev. 1990, 90, 879.
3. Arisawa, M.; Suwa, A.; Ashikawa, M.; Yamaguchi, M., ARKIVOC 2003, 8, 24.
4. (a) Takagi, J.; Sato, K.; Hartwig, J. F.; Ishiyama, T.; Miyaura, N., Tetrahedron Lett. 2002, 43, 5649.
5. (b) Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N.; Hartwig, J. F., J. Am. Chem. Soc. 2002, 124, 390.
6. (c) Takagi, J.; Sato, K.; Hartwig, J. F.; Ishiyama, T.; Miyaura, N., Tetrahedron Lett. 2002, 43, 5649.
7. (d) Ishiyama, T.; Takagi, J.; Yonekawa, Y.; Hartwig, J. F.; Miyaura, N., Adv. Synth. Catal. 2003, 345, 1103.
8. (e) Ishiyama, T.; Nobuta, Y.; Hartwig, J. F.; Miyaura, N., Chem. Commun. 2003, 2924.
9. (f) Boller, T. M.; Murphy, J. M.; Hapke, M.; Ishiyama, T.; Miyaura, N.; John F. Hartwig, J. Am. Chem. Soc. 2005, 127, 14263.
10. (a) Iverson, C. N.; Smith, M. R., III, J. Am. Chem. Soc. 1999, 121, 7696.
11. (b) Cho, J. Y.; Iverson, C. N.; Smith, M. R., J. Am. Chem. Soc. 2000, 122, 12868.
12. (a) Cho, J. Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E.; Smith, M. R., Science 2002, 295, 305.
13. (b) Chotana, G. A.; Rak, M. A.; Smith, M. R., J. Am. Chem. Soc. 2005, 127, 10539.
14. Maleczka, R. E.; Shi, F.; Holmes, D.; Smith, M. R., J. Am. Chem. Soc. 2003, 125, 7792.
15. Holmes, D.; Chotana, G. A.; Maleczka, R. E., Jr., Org. Lett. 2006, 8, 1407.
16. Tzschucke, C. C.; Murphy, J. M.; Hartwig, J. F., Org. Lett. 2007, 9, 761.
17. Murphy, J. M.; Tzschucke, C. C.; Hartwig, J. F., Org. Lett. 2007, 9, 757.
18. Thompson, A. L. S.; Kabalka, G. W.; Akula, M. R.; Huffman, J. W., Synthesis 2005, 4, 547.
19. (a) Kabalka, G. W.; Mereddy, A. R., Organometallics 2004, 23, 4519.
20. (b) Theibes, C.; Praskash, G. K. S.; Petasis, N. A.; Olah, G. A., Synlett 1998, 2, 141.
21. Szumigala, R. H. J.; Devine, P. N.; Gauthier, D. R. J.; Volante, R. P., J. Org. Chem. 2004, 69, 566.
22. (a) Matteson, D. S.; Kim, G. Y., Org. Lett. 2002, 4, 2153.
23. (b) Yuen, A. K. L.; Hutton, C. A., Tetrahedron Lett. 2005, 46, 7899.
24. (c) Lawrence, J. D.; Takahashi, M.; Bae, C.; Hartwig, J. F., J. Am. Chem. Soc. 2004, 126, 15334.
25. (a) McDonald, I. A.; Cosford, N. D. P.; Vernier, J. M., Annu. Rep. Med. Chem. 1995, 30, 41.
26. (b) McDonald, I. A.; Vernier, J. M.; Cosford, N. D. P.; Corey-Naeve, J., Curr. Pharm. Des. 1996, 2, 357.
27. Dukat, M.; Ramunno, A.; Banzi, R.; Damaj, M. I.; Martin, B.; Glennon, R. A., Bioorg. Med. Chem. Lett. 2005, 15, 4308.
28. Wagner, F. F.; Comins, D. L., J. Org. Chem. 2006, 71, 8673.
29. Cosford, N. D. P.; et al. J. Med. Chem. 1996, 39, 3235.