Iron(III) chloride catalyzed oxidative coupling of aromatic nuclei (Joc The Journal of Organic Chemistry (2004) 6 (913-916))

Journal of Organic Chemistry

Volumn 74, Issue 2, 2009, Pages 935-938

  Wang, Kailiang ^a   Lü, Maoyun ^a   Zhu, Xiaoqing ^a   Wang, Qingmin ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2-NAPHTHOLS; CATALYZED COUPLINGS; IRON CHLORIDES; ORGANIC CHEMISTRIES; OXIDATIVE COUPLINGS; PHENOL ETHERS; ROOM TEMPERATURES;

CHLORINE COMPOUNDS; ETHERS; PHENOLS;

IRON COMPOUNDS;

2 NAPHTHOL; 3 CHLOROPERBENZOIC ACID; ETHER; FERROUS CHLORIDE; PHENANTHRENE; PHENOL; 2-NAPHTHOL; 3-CHLOROPERBENZOIC ACID; CHLOROBENZOIC ACID DERIVATIVE; ETHER DERIVATIVE; FERRIC CHLORIDE; FERRIC ION; NAPHTHOL DERIVATIVE; OXIDIZING AGENT;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ELECTRON SPIN RESONANCE; MOLECULAR INTERACTION; MOLECULAR MECHANICS; OXIDATION; REACTION ANALYSIS; ROOM TEMPERATURE; STEREOSPECIFICITY; SUBSTITUTION REACTION; SYNTHESIS; CHEMISTRY; OXIDATION REDUCTION REACTION;

CATALYSIS; CHLOROBENZOATES; ETHERS; FERRIC COMPOUNDS; NAPHTHOLS; OXIDANTS; OXIDATION-REDUCTION; PHENOL;

EID: 60849096664     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8021633     Document Type: Article

References (38)

1. Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1470.
2. Gellert, E. J. Nat. Prod. 1982, 45, 50-73.
3. Li, Z. G.; Jin, Z.; Huang, R. Q. Synthesis 2001, 16, 2365-2378.
4. (a) Suffness, M.; Cordell, G. A. The Alkaloids. Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press, Orlando, FL, 1985; Vol. 25, pp 3 -355.
5. (b) Jin, Z.; Li, Z. G.; Huang, R. Q. Nat. Prod. Rep. 2002, 19, 454-476.
6. (a) Kim, S.; Lee, J.; Lee, T.; Park, H.; Kim, D. Org. Lett. 2003, 5, 2703-2706.
7. (b) Kim, S.; Lee, T.; Lee, E.; Lee, J.; Fan, G.; Lee, S.; Kim, D. J. Org. Chem. 2004, 69, 3144-3149.
8. (c) Camacho-Davila, A.; Herndon, J. W. J. Org. Chem. 2006, 71, 6682-6685.
9. (d) Ihara, M. Chem. Pharm. Bull. 2006, 54, 765-774.
10. (e) Furstner, A.; Kennedy, J. W. J. Chem~Eur. J. 2006, 12, 7398-7410.
11. (f) Kim, S.; Lee, Y.; Lee, M.; Lee, J.; Fu, T.; Song, Y.; Cho, Y.; Kim, J. D. J. Org. Chem. 2007, 72, 4886-4891.
12. (a) Taylor, E. C.; Andrade, J. G.; Rall, G. J. H.; Mckillop, A. J. Am. Chem. Soc. 1980, 102, 6513-6519.
13. (b) Mckillop, A.; Turrell, A. G.; Young, D. W.; Taylor, E. C. J. Am. Chem. Soc. 1980, 102, 6504-6512.
14. (c) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977-991.
15. Feldman, K. S.; Ensel, S. M. J. Am. Chem. Soc. 1994, 116, 3357-3366.
16. (a) Halton, B.; Maidment, A. I.; Officer, D. L.; Warner, J. M. Aust. J. Chem. 1984, 37, 2119-2128.
17. (b) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426-6427.
18. (c) Li, H.; Hu, T. S.; Wang, K. L.; Liu, Y. X.; Fan, Z. J.; Huang, R. Q.; Wang, Q. M. Lett. Org. Chem. 2006, 3, 806-810.
19. (d) Wang, K. L.; Wang, Q. M.; Huang, R. Q. J. Org. Chem. 2007, 72, 8416-8421.
20. (a) Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046-4048.
21. (b) Campeau, L. C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581-590.
22. (c) Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754-8756.
23. (a) Li, Z. P.; Li, C. J. J. Am. Chem. Soc. 2004, 126, 11810-11811.
24. (b) Li, Z. P.; Li, C. J. Org. Lett. 2004, 6, 4997-4999.
25. (c) Li, Z. P.; Li, C. J. J. Am. Chem. Soc. 2005, 127, 6968-6969.
26. (d) Li, Z. P.; Li, C. J. J. Am. Chem. Soc. 2005, 127, 3672-3673.
27. (e) Li, Z. P.; Li, C. J. J. Am. Chem. Soc. 2006, 128, 56-57.
28. Li, Z. P.; Cao, L.; Li, C. J. Angew. Chem., Int. Ed. 2007, 46, 6505-6507.
29. (a) Shilov, A. E.; Sful'pin, G. B. Chem. Rev. 1997, 97, 2879-2932.
30. (b) Matsushita, M.; Kamata, K.; Yamaguchi, K.; Mizuno, N. J. Am. Chem. Soc. 2005, 127, 6632-6640.
31. (c) Hull, K. L.; Lanni, E. L.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 14047-14049.
32. (a) Bolm, C.; Legros, J.; Paih, J. L.; Zani, L. Chem. Rev. 2004, 104, 6217-6254.
33. (b) Diaz, D. D.; Miranda, P. O.; Padron, J. I.; Martin, V. S. Curr. Org. Chem. 2006, 10, 457-476.
34. (c) Toda, F.; Tanaka, K.; Iwata, S. J. Org. Chem. 1989, 54, 3007-3009.
35. (d) Ding, K. L.; Wang, Y.; Zhang, L. J.; Wu, Y. J. Tetrahedron 1996, 52, 1005-1010.
36. (e) Li, T. S.; Duan, H. Y.; Li, B. Z.; Tewari, B. B.; Li, S. H. J. Chem. Soc., Perkin Trans. 1 1999, 1, 291-294.
37. Wang, K. L.; Lü, M. Y.; Wang, Q. M.; Huang, R. Q. Tetrahedron 2008, 64, 7504-7510.
38. Jin, Z.; Wang, Q. M.; Huang, R. Q. Synth. Commun. 2004, 34, 119-128.