General, mild, and intermolecular Ullmann-type synthesis of diaryl and alkyl aryl ethers catalyzed by diol-copper(I) complex

Journal of Organic Chemistry

Volumn 74, Issue 10, 2009, Pages 3675-3679

  Naidu, Ajay B ^a   Jaseer, E A ^a   Sekar, Govindasamy ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL ARYL ETHERS; ARYL BROMIDES; ARYLATION; BOND FORMATION; CATALYST LOADINGS; CATALYTIC AMOUNTS; CATALYTIC SYSTEM; CHEMICAL EQUATIONS; COPPER COMPLEXES; COUPLING REACTION; DIARYL ETHERS; MILD REACTION CONDITIONS; REACTION CONDITIONS; REACTION TEMPERATURE; TYPE SYNTHESIS;

ALKYLATION; BROMINE COMPOUNDS; CHEMICAL BONDS; ETHERS; FUNCTIONAL GROUPS; PHENOLS; SYNTHESIS (CHEMICAL);

COPPER COMPOUNDS;

ALCOHOL; BROMINE DERIVATIVE; COPPER COMPLEX; ETHER DERIVATIVE; FUNCTIONAL GROUP; PHENOL;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; SYNTHESIS; TEMPERATURE; ULLMANN COUPLING;

ACETONITRILES; ALCOHOLS; ANTHRACENES; CATALYSIS; COPPER; ETHERS; LIGANDS; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; TEMPERATURE;

EID: 65949123348     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900438e     Document Type: Article

References (42)

1. (a) Theil, F. Angew. Chem., Int. Ed. 1999, 38, 2345-2347.
2. (b) Zhu, J. Synlett 1997, 133-144.
3. (c) Boger, D. L.; Patane, M. A.; Zhou, J. J. Am. Chem. Soc. 1994, 116, 8544-8546.
4. (a) Yamazaki, N.; Washio, I.; Shibasaki, Y.; Mitsuru Ueda, M. Org. Lett. 2006, 8, 2321-2324.
5. (b) Asano, M.; Inoue, M.; Katoh, T. Synlett 2005, 2599-2602.
6. (c) Jiang, H.; Leger, J.-M.; Huc, I. J. Am. Chem. Soc. 2003, 125, 3448-3449.
7. (d) Bolm, C.; Hildebrand, J. P.; Muñiz, K.; Hermanns, N. Angew. Chem., Int. Ed. 2001, 40, 3284-3308.
8. (e) Gu, W. X.; Jing, X. B.; Pan, X. F.; Chan, A. S. C.; Yang, T. K. Tetrahedron Lett. 2000, 41, 6079-6082.
9. (f) Matsumoto, Y.; Uchida, W.; Nakahara, H.; Yanagisawa, I.; Shibanuma, T.; Nohira, H. Chem. Pharm. Bull. 2000, 48, 428.
10. (g) Cao, B.; Park, H.; Joullie, M. M. J. Am. Chem. Soc. 2002, 124, 520-521.
11. (h) Temal-Laïb, T.; Chastanet, J.; Zhu, J. J. Am. Chem. Soc. 2002, 124, 583-590.
12. Kawata, S.; Hirama, M. Tetrahedron Lett. 1998, 39, 8707-8710.
13. Sawyer, J. S. Tetrahedron 2000, 56, 5045-5065.
14. For some recent reports on palladium-catalyzed aryl ether synthesis, see: (a) Vorogushin, A. V.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 8146-8149.
15. (b) Kataoka, N.; Shelby, Q.; Stambuli, J.; Hartwig, J. J. Org. Chem. 2002, 67, 5553-5566.
16. (c) Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041-2075.
17. (d) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395-3396.
18. (a) Hartwig, J. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
19. (b) Shelby, Q.; Kataoka, N.; Mann, G.; Hartwig, J. J. Am. Chem. Soc. 2000, 122, 10718-10719.
20. (c) Karen, E. T.; Xiaohua, H.; Cynthia, A. P.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 10770-10771.
21. (d) Kuwabe, S.; Torraca, K. E.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 12202-12206.
22. (a) Lindley, J. Tetrahedron 1984, 40, 1433-1456.
23. (b) Paul, S.; Gupta, M. Tetrahedron Lett. 2004, 45, 8825-8829.
24. Marcoux, J. F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539-10540.
25. Wolter, M.; Nordmann, G.; Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 973-976.
26. Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315-4317.
27. Gujadhur, R. K.; Venkataraman, D. Synth. Commun. 2001, 31, 2865-2879.
28. Buck, E.; Song, Z. J.; Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 1623-1626.
29. Chen, Y. J.; Chen, H. H. Org. Lett. 2006, 8, 5609-5612.
30. Zhao, Y.; Wang, Y.; Sun, H.; Li, L.; Zhang, H. Chem. Commun. 2007, 3186-3188.
31. Miao, T.; Wang, L. Tetrahedron Lett. 2007, 48, 95-99.
32. Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940.
33. Ma, D.; Cai, Q. Org. Lett. 2003, 5, 3799-3802.
34. Cristau, H. J. A.; Pascal, P. C.; Hamada, S.; Francis, J. S.; Taillefer, M. Org. Lett. 2004, 6, 913-916.
35. Lv, X.; Bao, W. J. Org. Chem. 2007, 72, 3863-3867.
36. Jiajai, N.; Zhou, H.; Li, Z.; Xu, J.; Hu, S. J. Org. Chem. 2008, 73, 7814-7817.
37. Bistri, O.; Correa, A.; Bolm, C. Angew. Chem.Int. Ed. 2008, 47, 586-588.
38. Xia, N.; Taillefer, M. Chem. - Eur. J. 2008, 14, 6037-6039.
39. (a) Naidu, A. B.; Raghunath, O. R.; Prasad, D. J. C.; Sekar, G. Tetrahedron Lett. 2008, 49, 1057-1061.
40. (b) Naidu, A. B.; Sekar, G. Tetrahedron Lett. 2008, 49, 3147-3151.
41. Diol ligand L3 was easily synthesized from known literature procedure. See Supporting Information for experimental details.
42. Siegman, J. R.; Houser, J. J. J. Org. Chem. 1982, 47, 2773-2779.