Palladium-Catalyzed Amination of Aryl Halides: Mechanism and Rational Catalyst Design

Synlett

Volumn 1997, Issue 4, 1997, Pages 329-340

  Hartwig, John F ^a,b,c,d,e  

^a YALE UNIVERSITY   (United States)

^b PRINCETON UNIVERSITY   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d Yale   (United States)

^e ALFRED P SLOAN FOUNDATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1842740801     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-789     Document Type: Article

References (97)

1. One reaction of this type is the hydroamination of alkenes and alkynes. For leading references see the following 9 citations:
2. Catalysis with a low valent arylamido complex has been reported, although turnover numbers are not high: Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738-6744 and references therein.
3. Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 4108-4109.
4. Gagné, M. R.; Nolan, S. P.; Marks, T. J. Organometallics 1990, 9, 1716-1718.
5. Brunet, J.; Commenges, G.; Neibecker, D.; Philippot, K. J. Organomet. Chem. 1994, 469, 221.
6. Pez, G. P.; Galle, J. E. Pure Appl. Chem. 1985, 57, 1917-1926.
7. Hegedus, L. S.; Allen, G. F.; Bozell, J. J.; Waterman, E. L. J. Am. Chem. Soc. 1978, 100, 5800.
8. Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708.
9. Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753.
10. McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459.
11. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, 1987.
12. Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708.
13. Barañano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937.
14. Matsunaga, P. T.; Hillhouse, G. L.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 2075.
15. Matsunaga, P. T.; Mavropoulos, J. C.; Hillhouse, G. L. Polyhedron 1995, 14, 175.
16. Koo, K.; Hillhouse, G. L.; Rheingold, A. L. Organometallics 1995, 14, 456-460.
17. Koo, K.; Hillhouse, G. L. Organometallics 1995, 14, 4421.
18. Villanueva, L. A.; Abboud, K. A.; Boncella, J. M. Organometallics 1994, 13, 3921.
19. Komiya, S.; Akai, Y.; Tanaka, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1985, 4, 1130-1136.
20. Thompson, J. S.; Randall, S. L.; Atwood, J. L. Organometallics 1991, 10, 3906-3910.
21. Fryzuk, M. D.; Montgomery, C. D. Coord. Chem. Rev. 1989, 95, 1-40.
22. Bryndza, H.; Tam, W. Chem. Rev. 1988, 88, 1163-1188.
23. A similar relationship between H-X and M-X bond strengths was observed for late metal terminal arylamides: Bryndza, H. E.; Fong, L. K.; Paciello, R. A.; Tam, W.; Bercaw, J. E. J. Am. Chem. Soc. 1987, 109, 1444-1456.
24. Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. Organometallics 1991, 10, 1875-1887.
25. Roundhill, D. M. Chem. Rev. 1992, 92, 1-27.
26. Milstein, D.; Calabrese, J. C.; Williams, I. D. J. Am. Chem. Soc. 1986, 108, 6387-6389 and references therein.
27. Bryan, E. G.; Johnson, B. F. G.; Lewis, J. J. Chem. Soc., Dalton Trans. 1977, 1328-1330.
28. Koelliker, v.-R.; Milstein, D. Angew. Chem. Int. Ed. Engl. 1991, 30, 704-706.
29. Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. Inorg. Chem. 1987, 26, 973.
30. An exception is the activation of benzylamine: Glueck, D. S.; Newman Winslow, L. J.; Bergman, R. G. Organometallics 1991, 10, 1462-1479.
31. Suss-Fink, G. Z. Naturforsch. 1980, 35B, 454-457.
32. Alcock, N. W.; Bergamini, P.; Kemp, T. J.; Pringle, P. G.; Sostero, S.; Traverso, O. Inorg. Chem. 1991, 30, 1594.
33. A recent review of these data is the following: Brown, J. M.; Cooley, N. A. Chem. Rev. 1988, 88, 1031.
34. Mitchell, T. N. Synthesis 1992, 803.
35. Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551-564.
36. Kumada, M. Pure Appl. Chem. 1980, 52, 669.
37. Corriu, R. J. P.; Masse, J. P. J. Chem. Soc., Chem. Commun. 1972, 144.
38. Negishi, E. Acc. Chem. Res. 1982, 15, 340-348.
39. Kosugi, M.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 1423.
40. Kosugi, M.; Shimizu, Y.; Migita, T. J. Organomet. Chem. 1977, 129, C36.
41. Stille, J. K. Angew. Chem. Int. Ed. Engl. 1986, 25, 508.
42. Stille, J. K. Pure Appl. Chem. 1985, 57, 1771-1780.
43. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
44. Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927-928.
45. Kosugi, M.; Kameyama, M.; Sano, H.; Migita, T. Nippon Kagaku Kaishi 1985, 3, 547-551.
46. Boger, D. L.; Duff, S. R.; Panek, J. S.; Yasuda, M. J. Org. Chem. 1985, 50, 5782.
47. Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901.
48. Jones, K.; Lappert, M. F. J. Chem. Soc. 1965, 1944.
49. Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
50. Cristau, H. J.; Chabaud, B.; Chéne, A.; Christel, H. Synthesis 1981, 892.
51. Cristau, H. J.; Chabaud, B.; Labaudiniere, R.; Christol, H. J. Org. Chem. 1986, 51, 875.
52. Dickens, M. J.; Gilday, J. P.; Mowlem, T. J.; Widdowson, D. A. Tetrahedron 1991, 47, 8621-8634.
53. Murahashi, S.; Yamamura, M.; Yanagisawa, K.; Mita, N.; Kondo, K. J. Org. Chem. 1979, 44, 2408.
54. Takagi, K. Chem. Lett. 1987, 2221.
55. Takagi, K. Chem. Lett. 1985, 1307.
56. Migita, T.; Shimiza, T.; Asami, Y.; Shiobara, J.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385.
57. Kosugi, M.; Shimizu, T.; Migita, T. Chem. Lett. 1978, 13.
58. Yamamoto, T.; Sekine, Y. Inorg. Chim. Acta. 1984, 83, 47.
59. Kosugi, M.; Ogata, T.; Terada, M.; Sano, H.; Migita, T. Bull. Chem. Soc. Jpn. 1985, 58, 3657-3658.
60. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699-2702.
61. Ishiyama, T.; Mori, M.; Miyaura, N.; Suzuki, A. unpublished results disclosed in Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
62. Lindley, J. Tetrahedron 1984, 40, 1433-1456.
63. Paine, A. J. J. Am. Chem. Soc. 1987, 109, 1496-1502.
64. Anton, D. R.; Crabtree, R. H. Organometallics 1983, 2, 855-859.
65. 2 and in low yields. Enomoto, S.; Wada, H., Nishida, S.; Mukaida, Y.; Yanaka, M.; Takita, H. Jpn. Kokai Tokkyo Koho 1978, JP 53144552, 7pp.
66. Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969.
67. Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030.
68. Davis, A.; Hartwig, J. F. 1996, manuscript in preparation.
69. Saunders, M.; Telkowski, L.; Kates, M. R. J. Am. Chem. Soc. 1977, 99, 8070-8071.
70. Brookhart, M.; Green, M. L. H. J. Organomet. Chem. 1983, 250, 395.
71. A recent synopsis of these mechanisms and their accompanying data is included in: Amatore, C.; Pfluger, F. Organometallics 1990, 9, 2276-2282.
72. Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373.
73. Louie, J.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 11598.
74. Hegedus, L. S. In Transition Metals in the Synthesis of Complex Organic Molecules University Science Books: Mill Valey, CA, 1994; pp 90.
75. Cristau, H. J.; Chabaud, B.; Chéne, A.; Christol, H. Synthesis 1981, 892-894.
76. Takagi, K. Chem. Lett. 1987, 2221-2224.
77. Louie, J.; Paul, F.; Hartwig, J. F. submitted.
78. Cowan, R. L.; Trogler, W. C. J. Am. Chem. Soc. 1989, 111, 4750-4761.
79. Hartwig, J. F.; Richards, S.; Barañano, D.; Paul, F. J. Am. Chem. Soc. 1996, 3626.
80. A tin-free system has also been developed. Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609.
81. Wiegelmann-Kreiter, J. E. C.; Enkelmann, V.; Bunz, U. H. F. Chem. Ber. 1995, 128, 1055-1058.
82. Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 4708.
83. Grushin, V. V.; Alper, H. Organometallics 1993, 12, 1890-1901.
84. Lowry, T. H.; Richardson, T. H. In; second ed. Harper and Row, Publishers: New York, 1981; pp 146.
85. Maher, J. M.; Beatty, R. P.; Cooper, N. J. Organometallics 1985, 4, 1354.
86. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456-463.
87. Lowry, T. H.; Richardson, T. H. In Mechanism and Theory in Organic Chemistry; second ed. Harper and Row, Publishers: New York, 1981; pp 130-145.
88. Connors, K. A. In Chemical KineticsVCH Publishers, Inc.: New York, 1990; pp 315-328 and references therein.
89. Ozawa, F.; Kurihara, K.; Fujimori, M.; Hidaka, T.; Toyoshima, T.; Yamamoto, A. Organometallics 1989, 8, 180-188.
90. Ehrenson, S.; Brownlee, R. T. C.; Taft, R. W. Prog. Phys. Org. Chem. 1973, 10, 1.
91. Wells, P. R.; Ehrenson, S.; Taft, R. W. Prog. Phys. Org. Chem. 1968, 6, 147.
92. Calhorda, M. J.; Brown, J. M.; Cooley, N. A. Organometallics 1991, 10, 1431.
93. Mann, G.; Hartwig, J. 1996, in preparation.
94. Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848.
95. Driver, M. S.; Hartwig, J. F. 1996, submitted.
96. Louie, J.; Hartwig, J. F. 1996, submitted.
97. Jiang, Q.; Carroll, P. J.; Berry, D. H. Organometallics 1991, 10, 3648.