Copper-catalyzed arene C-H bond cross-coupling

Chemical Communications

Volumn , Issue 42, 2009, Pages 6433-6435

  Do, Hien Quang ^a   Daugulis, Olafs ^a  

^a University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; HYDROGEN; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; HALOGENATION; HYDROGEN BOND; IODINATION; SYNTHESIS;

EID: 70350325423     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b912890e     Document Type: Article

References (37)

1. J. Hassan M. Sévignon C. Gozzi E. Schulz M. Lemaire Chem. Rev. 2002 102 1359
2. F. Ullmann J. Bielecki Chem. Ber. 1901 34 2174
3. W. Steinkopf R. Leitsmann K. H. Hofmann Liebigs Ann. Chem. 1941 546 180
4. J. W. Sease L. Zechmeister J. Am. Chem. Soc. 1947 69 270
5. D. Ma F. Liu Chem. Commun. 2004 1934
6. K. Kamata S. Yamaguchi M. Kotani K. Yamaguchi N. Mizuno Angew. Chem., Int. Ed. 2008 47 2407
7. S. Usui Y. Hashimoto J. V. Morey A. E. H. Wheatley M. Uchiyama J. Am. Chem. Soc. 2007 129 15102
8. G. Brasche S. L. Buchwald Angew. Chem., Int. Ed. 2008 47 1932
9. Y. Zhang C.-J. Li Angew. Chem., Int. Ed. 2006 45 1949
10. X. Chen X.-S. Hao C. E. Goodhue J.-Q. Yu J. Am. Chem. Soc. 2006 128 6790
11. Z. Li L. Cao C.-J. Li Angew. Chem., Int. Ed. 2007 46 6505
12. R. J. Phipps N. P. Grimster M. J. Gaunt J. Am. Chem. Soc. 2008 130 8172
13. L. S. Liebeskind H. Yang H. Li Angew. Chem., Int. Ed. 2009 48 1417
14. S. Yotphan R. G. Bergman J. A. Ellman Org. Lett. 2009 11 1511
15. L. Ackermann H. K. Potukuchi D. Landsberg R. Vicente Org. Lett. 2008 10 3081
16. X. Chen G. Dobereiner X.-S. Hao R. Giri N. Maugel J.-Q. Yu Tetrahedron 2009 65 3085
17. T. Yoshizumi H. Tsurugi T. Satoh M. Miura Tetrahedron Lett. 2008 49 1598
18. H.-Q. Do O. Daugulis J. Am. Chem. Soc. 2007 129 12404
19. H.-Q. Do O. Daugulis J. Am. Chem. Soc. 2008 130 1128
20. H.-Q. Do R. M. K. Khan O. Daugulis J. Am. Chem. Soc. 2008 130 15185
21. K.-i. Fujita M. Nonogawa R. Yamaguchi Chem. Commun. 2004 1926
22. Y. Fuchita H. Oka M. Okamura Inorg. Chim. Acta 1992 194 213
23. M. Tani S. Sakaguchi Y. Ishii J. Org. Chem. 2004 69 1221
24. T. Jintoku Y. Fujiwara I. Kawata T. Kawauchi H. Taniguchi J. Organomet. Chem. 1990 385 297
25. L. J. Ackerman J. P. Sadighi D. M. Kurtz J. A. Labinger J. E. Bercaw Organometallics 2003 22 3884
26. S. Proch R. Kempe Angew. Chem., Int. Ed. 2007 46 3135
27. K. L. Hull M. S. Sanford J. Am. Chem. Soc. 2007 129 11904
28. G. Brasche J. Garcia-Fortanet S. L. Buchwald Org. Lett. 2008 10 2207
29. T. A. Dwight N. R. Rue D. Charyk R. Josselyn B. DeBoef Org. Lett. 2007 9 3137
30. D. R. Stuart K. Fagnou Science 2007 316 1172
31. A. Michael L. M. Norton Ber. Dtsch. Chem. Ges. 1878 11 107
32. B. Jones E. N. Richardson J. Chem. Soc. 1953 713
33. S. M. Hubig W. Jung J. K. Kochi J. Org. Chem. 1994 59 6233
34. 4, and concentrated under vacuum to a volume of about 2 mL. The mixture containing the product was subjected to flash chromatography on silica gel (hexanes followed by appropriate solvent to elute the products). After concentrating the fractions containing the product, the residue was dried under reduced pressure
35. R. Taylor, Electrophilic Aromatic Substitution, Wiley, Chichester, 1990
36. K. Shen Y. Fu J.-N. Li L. Liu Q.-X. Guo Tetrahedron 2007 63 1568
37. F. G. Bordwell Acc. Chem. Res. 1988 21 456