Intramolecular palladium-catalyzed aryl amination and aryl amidation

Tetrahedron

Volumn 52, Issue 21, 1996, Pages 7525-7546

  Wolfe, John P ^a   Rennels, Roger A ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINE; PIPERIDINE DERIVATIVE; PYRROLIDINE; UNCLASSIFIED DRUG;

CATALYSIS; CONFERENCE PAPER; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0029874188     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00266-9     Document Type: Conference Paper

References (64)

1. a) Boger, D.L.; Panek, J.S. Tetrahedron Lett. 1984, 25, 3175-3178.
2. b) Boger, D.L.; Duff, S.R.; Panek, J.S.; Yasuda, M.J. J. Org. Chem. 1985, 50, 5782-5789.
3. c) Boger, D.L.; Duff, S.R.; Panek, J.S., Yasuda, M.J. J. Org. Chem. 1985, 50, 5790-95.
4. a) Kametani, T.; Takahashi, K.; Ihara, M.; Fukumoto, K. J. Chem. Soc. Perkin 1 1976, 389-393.
5. b) Kametani, T.; Ohsawa, T.; Ihara, M.; Fukumoto, K. J. Chem. Soc. Perkin 1 1978, 460-464.
6. c) Kametani, T.; Ohsawa, T.; Ihara, M. Heterocycles 1980, 14, 277-280.
7. d) Lindley, J. Tetrahedron 1984, 40, 1433-1456.
8. Huisgen, R.; König, H.; Lepley, A.R. Chem. Ber. 1960, 93, 1496-1506.
9. b) Bunnett, J.F.; Hrutfiord, B.F. J. Am. Chem. Soc. 1961, 83, 1691-1697.
10. c) Heaney, H. Chem. Rev. 1962, 62, 81-97.
11. Ciganek, E. J. Org. Chem. 1992, 57, 4521-4527.
12. Hawes, E.M.; Davis, H.L. J. Heterocycl. Chem. 1973, 10, 39-42.
13. b) Pozharski, A.F.; Simonov, A.M.; Doronkin, V.N. Russ. Chem. Rev. 1978, 47, 1042-1060.
14. a) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993, 49, 49-64.
15. b) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993, 49, 3325-3342.
16. c) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron Lett. 1993, 34, 2937-2940.
17. For a review on transition metal-mediated approaches to the indole nucleus see: Hegedus, L.S. Angew. Chem. Int. Ed. Engl. 1988, 27, 1113-1126.
18. Collman, J.P.; Hegedus, L.S.; Norton, J.R.; Finke, R.G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987, pp 717-720.
19. a) Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927-928.
20. b) Guram, A.S.; Buchwald, S.L. J. Am. Chem. Soc. 1994, 116, 7901-7902.
21. c) Guram, A.S.; Rennels, R.A.; Buchwald, S.L. Angew. Chem. Int. Ed. Engl. 1995, 34, 1348-1350.
22. Hartwig has also reported the coupling of amines with aryl halides in the absence of a main group element: Hartwig, J.F.; Louie, J. Tetrahedron Lett. 1995, 36, 3609-3612.
23. Pd/C has been demonstrated to function as a catalyst in other Pd mediated coupling reactions: a) Roth, G.P.; Farina, V. Tetrahedron Lett. 1995, 36, 2191-2194.
24. b) Marck, G.; Villiger, A.; Buchecker, R. Tetrahedron Lett. 1994, 35, 3277-3280.
25. c) Guzman, A.; Velardi, E.; De la Rosa, M. Synth. Commun. 1990, 20, 2059.
26. Wolfe, J.P.; Buchwald, S.L. Submitted.
27. th ed.; John Wiley & sons: New York, 1992, pp 250-252.
28. For all three complexes, only the N-coordinated species could be detected. Widenhoefer, R.; Zhong, H.; Buchwald, S.L. Unpublished results.
29. Copper mediated Intermolecular coupling of amides with aryl halides at high temperatures has been reported: a) Yamamoto, T.; Ehara, Y.; Kubota, M.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1980, 53, 1 1299-1302.
30. b) Renger, B. Synthesis, 1985, 856-860.
31. 3.
32. 13 is ∼17. See King, J.F. in The Chemistry of Sulphonic Acids, Esters, and Their Derivatives; Patai, S.; Rapoport, Z. Eds.; John Wiley & Sons: West Sussex, 1991, pp 252-257.
33. 13 is ∼9-11. Zalewski, R.I. in The Chemistry of Acid Derivatives; Patai, S. Ed.; John Wiley & Sons, West Sussex, 1992, pp 357-365.
34. a) Gioria, J.M; Susz, B.P. Helv. Chim. Acta., 1971, 54, 2251-2256.
35. b) Wayland, B.; Schramm, R.F. Inorg. Chem. 1969, 8, 971.
36. Kiguchi, T.; Kuninobu, N.; Takahashi, Y.; Yoshida, Y.; Naito, T.; Ninomiya, I. Synthesis 1989, 778-781.
37. Thon, D.; Schneider, W. Chem. Ber. 1976, 109, 2743-2761.
38. Ito, Y.; Miyata, S.; Nakatsuka, M.; Saegusa, T. J. Am. Chem. Soc. 1981, 103, 5250-5251.
39. Meyers, A.I.; Milot, G. J. Org. Chem. 1993, 58, 6538-6540.
40. Buchwald, S.L.; Nielsen, R.B. Chem. Rev. 1988, 88, 1047-1058.
41. Mori, M.; Chiba, K.; Ban, Y. J. Org. Chem. 1978, 43, 1684-1687.
42. Nagarajan, K.; Nair, M.D.; Pillai, P.M. Tetrahedron 1967, 23, 1683-1690.
43. Combrisson, S.; Roques, B.P. Tetrahedron, 1976, 32, 1507-1516.
44. Fritz, H.; Winkler, T. Helv. Chim. Acta. 1976, 59, 903-907.
45. Beak, P.; Selling, G.M. J. Org. Chem. 1989, 54, 5574-5580.
46. Mon, M.; Kanda, N.; Oda, I.; Ban, Y. Tetrahedron 1985, 41, 5465-6474.
47. Doyle, M.P.; Shankin, M.S.; Pho, H.Q.; Mahapatro, S.N. J. Org. Chem. 1988, 53, 1017-1022.
48. Crestini, C.; Salasino, R. Syn. Commun. 1994, 24, 2835-2841.
49. Shono, T.; Kashimura, S.; Nogusa, H. Chem. Lett. 1986, 425-428.
50. Olah, G.A.; Balaram Gupta, B.G.; Narang, S.C. Sythesis, 1979, 274-276.
51. Oishi, T.; Kamata, K.; Sakado, K.; Ban, Y. J. Chem. Soc., Chem. Commun. 1972, 1148-1149.
52. Fisher, G.P.; Schultz, H.P. J. Org. Chem. 1974, 39, 635-640.
53. Texier-Boullet, F.; Foucaud, A. Synthesis, 1979, 884-885.
54. Nystrom, R.F. J. Am. Chem. Soc. 1955, 77, 2544-2545.
55. Jeffry, T. J. Chem. Soc., Chem Commun. 1984, 1287-1289.
56. Rieke, R.; Inaba, S. Synthesis, 1984, 842-844.
57. Koppang, M.D.; Ross, G.A.; Woolsey, N.F.; Bartak, D.E. J. Am. Chem. Soc. 1986, 108, 1441-1447.
58. A modification of Kadin's protocol was used for the reduction: Kadin, S. J. Org. Chem. 1966, 31, 620-622.
59. Brunet, J.J.; Sidot, C.; Caubere, P. J. Org. Chem. 1983, 48, 1166-1171.
60. Mori, M.; Ciba, K.; Inotsume, N.; Ban, Y. Heterocycles 1979, 12, 921-924.
61. Cooke, M.P.J.; Widener, R.K. J. Org. Chem. 1987, 52, 1381-1396.
62. Watt, D.S.; Adamczyk, M. J. Org. Chem. 1984, 49, 4227-4237.
63. Heck, R.F. Palladium Reagents in Organic Synthesis; Academic Press Inc.: Orlando, FL, 1985, p2.
64. Akagi, M.; Ozaki, K. Heterocycles 1987, 26, 61-64.