High-yielding intramolecular direct arylation reactions with aryl chlorides

Organic Letters

Volumn 7, Issue 9, 2005, Pages 1857-1860

  Campeau, Louis Charles ^a   Thansandote, Praew ^a   Fagnou, Keith ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIDE; HALIDE; IMIDAZOLE DERIVATIVE; INORGANIC SALT; PALLADIUM COMPLEX;

ADDITION REACTION; ARTICLE; ARYLATION; CATALYST; CHEMICAL REACTION;

EID: 18844443420     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050501v     Document Type: Article

References (42)

1. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
2. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. In Principles and Applications of Organotransition Metal Chemistry: University Science: Mill Valley, CA, 1987.
3. For example see: (a) Hillier, A. C.; Grasa, G. A.; Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. J. Organomet. Chem. 2002, 653, 69.
4. (b) Huang, J.; Nolan, S. P. J. Am. Chem. Soc. 1999, 121, 9889.
5. (c) Huang, J.; Grasa, G. A.; Nolan, S. P. Org. Lett. 1999, 1, 1307.
6. (d) Lee, H. M.; Nolan, S. P. Org. Lett. 2000, 2, 119.
7. (e) Grasa, G. A.; Viciu, M. S.; Huang, J.; Nolan, S. P. J. Org. Chem 2001, 66, 7729.
8. (f) Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan, S. P. Organometallics 2002, 21, 2866.
9. (g) Viciu, M. S.; Kissling, R. M.; Stevens, E. D.; Nolan S. P. Org. Lett. 2002, 4, 2229.
10. (h) Viciu, M. S.; Germaneau, R. F.; Navarro-Fernandez, O.; Stevens E. D.; Nolan, S. P. Organometallics 2002, 21, 5740.
11. (a) Viciu, M. S.; Navarro, O.; Germaneau, R. F.; Kelly, R. A., III; Sommer, W.; Marion, N.; Stevens, E. D.; Cavallo, L.; Nolan, S. P. Organometallics 2004, 23, 1629.
12. (b) Jensen, D. R.; Schultz, M. J.; Mueller, J. A.; Sigman, M. S. Angew. Chem., Int. Ed. 2003, 42, 3810.
13. (c) Frisch, A. C.; Rataboul, F.; Zapf, A.; Beller, M. J. Organomet. Chem. 2003, 687, 403.
14. (d) Viciu, M. S.; Stevens, E. D.; Petersen, J. L.; Nolan, S. P. Organometallics 2004, 23, 3752.
15. For a review, see: Crudden, C. M.; Allen, A. P. Coord. Chem. Rev. 2004, 248, 2247.
16. (a) Marshall, W. J.; Grushin, V. V. Organometallics 2003, 22, 1591.
17. (b) McGuinness, D. S.; Green, M. J.; Cavell, K. J.; Skeleton, B. W.; White, A. H. J. Organomet. Chem. 1998, 565, 165.
18. (c) McGuinness, D. S.; Cavell, K. J.; Skeleton, B. W.; White, A. H. Organometallics 1999, 18, 1596.
19. (d) Caddick, S.; Cloke, F. G. N.; Hitchcock, P. B.; Leonard, J.; Lewis, A. K.; McKerrecher, D.; Titcomb, L. R. Organometallics 2002, 21, 4318.
20. For recent reviews, see: (a) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
21. (b) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
22. (c) Miura, M.; Nomura, M. Top. Curr. Chem. 2002, 219, 211.
23. (d) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.
24. For recent intermolecular examples, see: (e) Sezen, B.; Sames D. J. Am. Chem. Soc. 2003, 125, 5274.
25. (f) Okazawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 5286.
26. (g) Bedford, R. B.; Coles, S. J.; Hursthouse, M. B.; Limmert, M. E. Angew. Chem., Int. Ed. 2003, 42, 112.
27. (h) Kakiuchi, F.; Kan, S.; Igi, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2003, 125, 1698.
28. For recent intramolecular examples, see: (i) Campo, M. A.; Huang, Q.; Yao, T.; Tian, Q.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 11506.
29. (j) Huang, Q.; Fazio, A.; Dai, G.; Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 7460.
30. (k) Liu, Z.; Larock, R. C. Org. Lett. 2004, 6, 3739.
31. (l) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2.
32. For our own work in this area, see: (a) Campeau, L.-C.; Parisien, M.; Leblanc, M.; Fagnou, K. J. Am. Chem. Soc. 2004, 126, 9186.
33. (b) Lafrance, M.; Blaquiere, N.; Fagnou, K. Chem. Commun. 2004, 24, 2874.
34. 9b (a) Rieth, R. D.; Mankad, N. P.; Calimano, E.; Sadighi, J. P. Org. Lett. 2004, 6, 3981.
35. (b) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2002, 2310. To our knowledge, no intramolecular examples with larger ring sizes have appeared.
36. For a review of palladium-catalyzed cross-coupling reactions of aryl chlorides, see: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
37. For experimental procedures, complete characterization, and X-ray crystal structures of all new palladium complexes, see Supporting Information.
38. Addition of [IPr]HCl to 3-IPr only leads to modest increases in TON.
39. This kind of TON increase upon NHC-HCl addition was also observed in telomerization of dienes with alcohols, but increased reaction rates were observed with higher imidazolium salt additive concentrations: Jackstell, R.; Harkal, S.; Jiao, H.; Spannenberg, A.; Borgmann, C.; Röttger, D.; Nierlich, F.; Elliot, M.; Niven, S.; Cavell, K.; Navarro, O.; Viciu, M. S.; Nolan, S. P.; Beller, M. Chem. Eur. J. 2004, 10, 3891
40. Knolker, H.-J.; Ready, K. R. Chem. Rev. 2002, 102, 4303.
41. Lebel, H.; Janes, M. K.; Charette, A. B.; Nolan, S. P. J. Am. Chem. Soc. 2004, 126, 5046-5047.
42. For a review, see: Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.