Proline/pipecolinic acid-promoted copper-catalyzed P-arylation

Journal of Organic Chemistry

Volumn 71, Issue 13, 2006, Pages 5020-5022

  Huang, Cheng ^a   Tang, Xu ^a   Fu, Hua ^a   Jiang, Yuyang ^a,b   Zhao, Yufen ^a  

^a Tsinghua University   (China)

^b TSINGHUA UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

COUPLING REACTIONS; ORGANOPHOSPHORUS COMPOUNDS; P-ARYLATION; PROLINE;

CATALYST ACTIVITY; COPPER; PHOSPHORUS COMPOUNDS; REACTION KINETICS;

AMINO ACIDS;

COPPER; ORGANOPHOSPHORUS COMPOUND; PHOSPHINE OXIDE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PIPECOLIC ACID DERIVATIVE; PIPECOLINIC ACID; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROLINE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; COUPLING REACTION; METHODOLOGY;

ALKYLATION; CATALYSIS; COPPER; HYDROCARBONS, HALOGENATED; IODIDES; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; PIPECOLIC ACIDS; PROLINE; STEREOISOMERISM;

EID: 33745466419     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060492j     Document Type: Article

References (55)

1. For reviews, see: (a) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 15, 2428.
2. (b) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
3. (c) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
4. For other related studies, see: (d) Okano, K.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2003, 5, 4987.
5. (e) Han, C.; Shen, R.; Su, S.; Porco, J. A., Jr. Org. Lett. 2004, 6, 27.
6. (f) Buck, E.; Song, Z. J.; Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 1623.
7. For some recent reports, see: (a) Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539.
8. (b) Buck, E.; Song, Z. J.; Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 1623.
9. (c) Palomo, C.; Oiarbide, M.; Lopez, R.; Gomez-Bengoa, E. Chem. Commun. 1998, 2091.
10. (d) Ma, D.; Cai, Q. Org. Lett. 2003, 5, 3799.
11. (e) Fagan, P. J.; Hauptman, E.; Shapiro, R.; Casalnuovo, A. J. Am. Chem. Soc. 2000, 122, 5043.
12. (f) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4135.
13. (g) Cristau, H. J.; Cellier, P. P.; Hamada, S.; Spindler, J. F.; Tailefer, M. Org. Lett. 2004, 6, 913.
14. (a) Hosseinzadeh, R.; Tajbakhsh, M.; Mohadjerani, M.; Alikarami, M. Synlett 2005, 1101.
15. (b) Wolter, M.; Nordmann, G.; Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 973.
16. (a) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
17. (b) Antilla, J. C.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684.
18. (c) Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Bchwald, S. L. J. Org. Chem. 2004, 69, 5578.
19. (a) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
20. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793.
21. (a) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459.
22. (b) Ma, D.; Xia, C. Org. Lett. 2001, 3, 2583.
23. (c) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
24. (d) Ma, D.; Cai, Q. Org. Lett. 2003, 5, 3799.
25. (e) Ma, D.; Cai, Q. Synlett 2004, 1, 128.
26. (f) Pan, X.; Cai, Q.; Ma, D. Org. Lett. 2004, 6, 1809.
27. (g) Zhu, W.; Ma, D. Chem. Commun. 2004, 888.
28. (h) Ma, D.; Liu, F. Chem. Commun. 2004, 1934.
29. (i) Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164.
30. (a) Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Eur. J. Org. Chem. 2004, 695.
31. (b) Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Chem. Eur. J. 2004, 10, 5607.
32. Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312.
33. Kelkar, A. A.; Patil, N. M.; Chaudhari, R. V. Tetrahedron Lett. 2002, 43, 7143.
34. Gajare, A. S.; Toyota, K.; Yoshifuji, M.; Yoshifuji, F. Chem. Commun. 2004, 1994.
35. Rao, H. H.; Fu, H.; Jiang, Y. Y.; Zhao, Y. F. J. Org. Chem. 2005, 70, 8107.
36. For a review, see: (a) Engel, R. In Handbook of Organophosphorus Chemistry; Engel, R., Ed.; Marcel Dekker: New York, 1992; Chapter 11.
37. (b) Wester, R. T.; Chambers, R. J.; Green, M. D.; Murphy, W. R. Bioorg. Med. Chem. Lett. 1994, 4, 2005.
38. (c) Hirschmann, R.; Smith, A. B., III; Taylor, C. M.; Benkovic, P. A.; Taylor, S. D.; Yager, K. M.; Sprengeler, P. A.; Benkovic, S. J. Science 1994, 265, 234.
39. (d) Oishi, S.; Karki, R. G.; Kang, S.-U.; Wang, X.; Worthy, K. M.; Bindu, L. K.; Nicklaus, M. C.; Fisher, R. J.; Burke, T. R., Jr. J. Med. Chem. 2005, 48, 764.
40. (e) Jiao, X.-Y.; Bentrude, W. G. J. Org. Chem. 2003, 68, 3303.
41. (a) Bestmann, H. J.; Vostrowsky, O. Top. Curr. Chem. 1983, 109, 85.
42. (b) Pommer, H.; Thieme, P. C. Top. Curr. Chem. 1983, 109, 165.
43. (c) Kallmerten, J.; Wittman, M. D. Tetrahedron Lett. 1986, 27, 2443.
44. (d) Xu, Y.; Li, Z.; Xia, J.; Guo, H.; Huang, Y. Synthesis 1984, 781.
45. (e) Dalpozzo, R.; De Nino, A.; Miele, D.; Tagarelli, A.; Bartoli, G. Eur. J. Org. Chem. 1999, 2299.
46. (a) Ogawa, T.; Usuki, N.; Ono, N. J. Chem. Soc., Perkin Trans. 1 1998, 2953.
47. (b) Gelman, D.; Jiang, L.; Buchwald, S. L. Org. Lett. 2003, 5, 2315.
48. (c) Van Allen, D.; Venkataraman, D. J. Org. Chem. 2003, 68, 4590.
49. (d) Thielges, S.; Bisseret, P.; Eustache, J. Org. Lett. 2005, 7, 681.
50. (e) Rao, H.; Jin, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Chem. Eur. J. 2006, 12, 3636.
51. (a) Zhu, W.; Ma, D. J. Org. Chem. 2005, 70, 2696.
52. (b) Xie, X.; Cai, G.; Ma, D. Org. Lett. 2005, 7, 4693.
53. Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 14844.
54. Zhou, T.; Chen, Z.-C. Synth. Commun. 2001, 31, 3289.
55. Montchamp, J.-L.; Dumond, Y. R. J. Am. Chem. Soc. 2001, 123, 510.