Formation of palladium bis (amine) complexes from reaction of amine with palladium tris(o-tolyl)phosphine mono(amine) complexes

Organometallics

Volumn 15, Issue 16, 1996, Pages 3534-3542

  Widenhoefer, Ross A ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000712049     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9603169     Document Type: Article

References (115)

1. Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348.
2. Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133.
3. See also: (a) Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609. (b) Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 20, 7525.
4. See also: (a) Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609. (b) Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 20, 7525.
5. (a) Stille, J. K. Angew. Chem., Int. Ed. Engt. 1986, 25, 508.
6. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
7. (c) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
8. 3 and BINAP effectively cross-couple aryl bromides with primary amines: Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc., in press.
9. Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969.
10. Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995,14, 3030.
11. (a) Loar, M. K.; Stille, J. K. J. Am. Chem. Soc. 1981, 103, 4174.
12. (b) Moravskiy, A.; Stille, J. K. J. Am. Chem. Soc. 1981, 103, 4182.
13. (c) Morrell, D. G.; Kochi, J. K. J. Am. Chem. Soc. 1975, 97, 7262.
14. (d) Ozawa, F.; Ito, T.; Yamamoto, A. J. Am. Chem. Soc. 1980, 102, 6457.
15. (e) McCarthy, T. J.; Nuzzo, R. G.; Whitesides, G. M. J. Am. Chem. Soc. 1981, 103, 1676.
16. (f) Komiya, S.; Albright, T. A.; Hoffmann, R.; Kochi, J. K. J. Am. Chem. Soc. 1976, 98, 7255.
17. (g) Komiya, S.; Albright, T. A.; Hoffmann, R.; Kochi, J. K. J. Am. Chem. Soc. 1977, 99, 8440.
18. (h) Tatsumi, K.; Hoffmann, R.; Yamamoto, A.; Stille, J. K. Bull. Chem. Soc. Jpn. 1981, 54, 1857.
19. Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373.
20. Widenhoefer, R. A.; Zhong, H. A.; Buchwald, S. L. Organometallics 1996, 15, 2745.
21. Widenhoefer, R. A.; Zhong, H. A.; Buchwald, S. L. Abstracts of Papers, 210th National Meeting of the American Chemical Society, Chicago, IL, Aug 1995; American Chemical Society: Washington, DC, 1995; INOR 70.
22. Widenhoefer, R. A.; Buchwald, S. L. Organometallics 1996, 15, 2755.
23. Kinetic studies have been performed: Widenhoefer, R. A.; Zhong, H. A.; Buchwald, S. L. Manuscript in preparation.
24. (a) Stephanson, T. A.; Morehouse, S. M.; Powell, A. R.; Heffer, J. P.; Wilkinson, G. J. Chem. Soc. 1965, 3632.
25. (b) Iball, J.; MacDougall, M.; Scrimgeour, S. Acta Crystallogr. 1975, B31, 1672.
26. (c) Goggin, P. L.; Goodfellow, R. J.; Reed, F. J. S. J. Chem. Soc., Dalton Trans. 1972, 1298.
27. (d) Shaplygin, I. S. Lazarev, V. B. Zh. Neorg. Khim. 1978, 23, 603.
28. (e) Mirskova, I. S.; Sytov, G. A.; Skanazarova, I. M.; Avakyan, V. G.; Perchenko, V. N.; Nametkin, N. S. Dokl. Akad. Nauk SSSR 1977, 237, 346.
29. (f) Mellor, J. W. A Comprehensive Treatise on Inorganic and Theoretical Chemistry; Longmans, Green: London, 1936; Vol. XV.
30. Coe, J. S.; Lyons, J. R. Inorg. Chem. 1970, 9, 1775.
31. (a) Lock, C. J. L.; Zvagulis, M. Inorg. Chem. 1981, 20, 1817.
32. (b) Iball, J.; Scrimgeour, S. N. Acta Crystallogr. 1977, B33, 1194.
33. (c) Lock, C. J. L.; Speranzini, R. A.; Zvagulis, M. Acta Crystallogr. 1980, B39, 1989.
34. (d) Lock, C. J. L.; Zvagulis, M. Acta Crystallogr. 1980, B36, 2140.
35. (a) Chatt, J.; Duncanson, L. A.; Venanzi, L. M. J. Inorg. Nucl. Chem. 1958, 8, 67.
36. (b) Chatt, J.; Duncanson, L. A.; Venanzi, L. M. J. Chem. Soc. 1955, 4461.
37. (c) Chatt, J.; Duncanson, L. A.; Venanzi, L. M. J. Chem. Soc. 1956, 2712.
38. Kollman, P. A.; Allen, L. C. Chem. Rev. 1972, 72, 283.
39. 1H NMR spectrum could also result from methanol-promoted halide dissociation.
40. Joesten, M. D.; Schaad, L. J. Hydrogen Bonding; Marcel Dekker: New York, 1974; p 173.
41. (a) Kegley, S. E.; Schaverien, C. J.; Freudenberger, J. H.; Bergman, R. G.; J. Am. Chem. Soc. 1987, 109, 6563.
42. (b) Osakada, K.; Kim, Y. J.; Yamamoto, A. J. Organomet. Chem. 1990, 382, 303.
43. (c) Kim, Y. J.; Osakada, K.; Takenaka, A.; Yamamoto, A. J. Am. Chem. Soc. 1990, 112, 1096,
44. (d) Osakada, K.; Kim, Y. J.; Tanaka, M.; Ishiguro, S. I.; Yamamoto, A. Inorg. Chem. 1991, 30, 404.
45. (e) Shubina, E. S.; Belkova, N. V.; Krylov, A. N.; Vorontsov, E. V.; Epstein, L. M.; Gusev, D. G.; Niedermann, M.; Berke, H. J. Am. Chem. Soc. 1996, 118, 1105.
46. (a) Deranleau, D. A. J. Am. Chem. Soc. 1969, 91, 4050.
47. (b) Deranleau, D. A. J. Am. Chem. Soc. 1969, 91, 4044.
48. (a) Seligson, A. L.; Trogler, W. C. J. Am. Chem. Soc. 1991, 113, 2520.
49. (b) The cone angle for methylbenzylamine has not been determined. A cone angle of ∼127° can be approximated by comparison to known cone angles for the related secondary amines HN(Me)Ph (126°) and NH(Me)-n-Pr (127°).
50. (a) Albert, A.; Serjeant, E. P. The Determination of Ionization Constants, 3rd ed.; Chapman and Hall: London, 1984.
51. (b) Smith, R. M.; Martell, A. E. Critical Stability Constants; Plenum Press: New York, 1989; Vol. 6, 2nd supplement.
52. (c) Perrin, D. D. Stability Constants of Metal-Ion Complexes: Part B-Organic Ligands; IUPAC Pergamon Press: London, 1979.
53. Thomas, K.; Osborn, J. A.; Powell, A. R.; Wilkinson, G. J. Chem. Soc. A 1968, 1801.
54. (a) Fujita, J.; Nakamoto, K.; Kobayashi, M. J. Chem. Soc. 1956, 3295.
55. (b) Sakaguchi, U.; Tamaki, S.; Tomioka, K.; Yoneda, H. Inorg. Chem. 1985, 24, 1624.
56. Chatt, J.; Leigh, G. J.; Thankarajan, N. J. Chem. Soc. A 1971, 3168.
57. (a) Andrews, M. A.; Kaesz, H. D. J. Am. Chem. Soc. 1979, 101, 7238.
58. (b) Andrews, M. A.; van Buskirk, G.; Knobler, C. B.; Kaesz, H. D. J. Am. Chem. Soc. 1979, 101, 7246.
59. (a) Massa, W.; Babel, D. Chem. Rev. 1988, 88, 275.
60. (b) Richmond, T. G. Coord. Chem. Rev. 1990, 105, 221.
61. (c) Lock, C. J. L.; Speranzini, R. A.; Zvagulis, M. Acta Crystallogr. 1980, B36, 1789.
62. (d) Alsters, P. L.; Boersma, J.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. Organometallics 1993, 12, 1639.
63. (a) Kapteijn, G. M.; Dervisi, A.; Grove, D. M.; Kooijman, H.; Lakin, M. T.; Spek, A.; van Koten, G. J. Am. Chem. Soc. 1995, 117, 10939.
64. (b) Kim, Y. J.; Choi, J. C.; Osakada, K. J. Organomet. Chem. 1995, 491, 97.
65. (c) Ozawa, F.; Yamagami, I.; Yamamoto, A. J. Organomet. Chem. 1994, 473, 265.
66. (d) Simpson, R. D.; Bergman, R. G. Organometallics 1993, 12, 781.
67. (e) Bugno, C. D.; Pasquali, M.; Leoni, P.; Sabatino, P.; Braga, D. Inorg. Chem. 1989, 28, 1390.
68. (f) Seligson, A. L.; Cowan, R. L.; Trogler, W. C. Inorg. Chem. 1991, 30, 3371.
69. (g) Osakada, K.; Kim, Y. J.; Tanaka, M.; Ishiguro, S. I.; Yamamoto, A. Inorg. Chem. 1991, 30, 197.
70. (h) Kapteijn, G. M.; Grove, D. M.; van Koten, G.; Smeets, W. J. J.; Spek, A. L. Inorg. Chim. Acta 1993, 207, 131.
71. (i) Osakada, K.; Ohshiro, K.; Yamamoto, A. Organometallics 1991, 10, 404.
72. (j) Canty, A. J.; Jin, H.; Skelton, B. J.; White, A. H. J. Organomet. Chem. 1995, 503, C16.
73. (k) Braga, D.; Grepioni, F.; Biradha, K.; Pedireddit, V. R.; Desiraju, G. R. J. Am. Chem. Soc. 1995, 117, 3156.
74. (l) Kapteijn, G. M.; Grove, D. M.; Kooijman, H.; Smeets, J. J.; Spek, A. L.; van Koten, G. Inorg. Chem. 1996, 35, 526.
75. (m) Kapteijn, G. M.; Grove, D. M.; Kooijman, H.; Smeets, J. J.; Spek, A. L.; van Koten, G. Inorg. Chem. 1996, 35, 534.
76. (a) Sutherland, B. R.; Cowie, M. Organometallics 1985, 4, 1637.
77. (b) Sartorelli, U.; Garlashelli, L.; Bonora, G. Inorg. Chim. Acta 1972, 5, 191.
78. Howard-Lock, H. E.; Lock, C. J. L.; Turner, G.; Zvagulis, M. Can. J. Chem. 1981, 59, 2737.
79. Lock, C. J. L.; Zvagulis, M. Inorg. Chem. 1981, 20, 1817.
80. Lock, C. J. L.; Speranzini, R. A.; Zvagulis, M. Acta Crystallogr. 1980, B36, 1789.
81. Fryzuk, M. D.; MacNeil, P. A.; Rettig, S. J. J. Am. Chem. Soc. 1987, 109, 2803.
82. Poss, M. J.; Arif, A. M.; Richmond, T. G. Organometallics 1988, 7, 1669.
83. Brammer, L.; Charnock, P. L.; Goggin, P. L.; Goodfellow, R. J.; Orpen, A. G.; Koetzle, T. F. J. Chem. Soc., Dalton Trans. 1991, 1789.
84. Cowan, R. L.; Trogler, W. C. J. Am. Chem. Soc. 1989, 111, 4750.
85. Alsters, P. L.; Baesjou, P. J.; Janssen, M. D.; Kooijman, H.; Sicherer-Roetman, A.; Spek, A. L.; van Koten, G. Organometallics 1992, 11, 4124.
86. Colquhoun, H. M.; Lewis, D. F.; Stoddart, J. F.; Williams, D. J. J. Chem. Soc., Dalton Trans. 1983, 607.
87. Atwood, J. L.; Darensbourg, D. J. Inorg. Chem. 1977, 16, 2314.
88. Cotton, F. A.; Darensbourg, D. J.; Fang, A.; Kolthammer, B. W. S.; Reed, D.; Thompson, J. L. Inorg. Chem. 1981, 20, 4090.
89. Li, M. P.; Drago, R. S.; Pribula, A. J. J. Am. Chem. Soc. 1977, 99, 6900.
90. (a) de Graaf, W.; Boersma, J.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. Organometallics 1989, 8, 2907.
91. (b) Wang, L.; Wang, C.; Bau, R.; Flood, T. C. Organometallics 1996, 15, 491.
92. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransiton Metal Chemistry; University Science: Mill Valley, CA, 1987; p 69.
93. Tolman, C. A. Chem. Rev. 1977, 77, 313.
94. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
95. (a) Gagne, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275.
96. (b) Baralt, E.; Smith, S. J.; Hurwitz, J.; Horvath, I. T.; Fish, R. H. J. Am. Chem. Soc. 1992, 114, 5187.
97. (c) Gray, S. D.; Smith, D. P.; Bruck, M. A. J. Am. Chem. Soc. 1992, 114, 5462.
98. (d) Fish, R. H.; Baralt, E.; Smith, S. J. Organometallics 1991, 10, 54.
99. (e) Satterfield, C. N. Heterogeneous Catalysis in Practice, 2nd ed.; McGraw-Hill: New York, 1991.
100. (f) Ball, G. E.; Cullen, W. R.; Fryzuk, M. D.; Henderson, W. J.; James, B. R.; MacFarlane, K. S. Inorg. Chem. 1994, 33, 1464.
101. (g) Volt, J.; Pasek, J. In Catalytic Hydrogenation: Studies in Surface Science and Catalysis; Cerverry, L., Ed.; Elsevier: Amsterdam, 1986; Vol. 27, Chapter 4.
102. (a) Canovese, L.; Visentin, F.; Uguagliati, P.; Di Bianca, F.; Antonaroli, S.; Crociani, B. J. Chem. Soc., Dalton Trans. 1994, 3113.
103. (b) Dennenberg, R. J.; Darensbourg, D. J. Inorg. Chem. 1972, 11, 72.
104. (c) Canovese, L.; Visentin, F.; Uguagliati, P.; Crociani, B.; Di Bianca, F. Inorg. Chim. Acta 1995, 235, 45.
105. (d) Uruska, I.; Zielkiewicz, J.; Szpakowska, M. J. Chem. Soc., Dalton Trans. 1990, 733.
106. (e) Therien, M. J.; Trogler, W. C. J. Am. Chem. Soc. 1987, 109, 5127.
107. (f) Burkey, T. J. Polyhedron 1989, 8, 2681.
108. (g) Uruska, I.; Zielkiewicz, J.; Szpakowska, M. J. Chem. Soc., Dalton Trans. 1990, 733.
109. (h) Brown, H. C. Boranes in Organic Chemistry; Cornell Univerisity Press: Ithaca, NY, 1972.
110. (i) Deeming, A. J.; Rothwell, I. P.; Hursthouse, M. B.; New, L. J. Chem. Soc., Dalton Trans. 1978, 1490.
111. (J) Odell, A. L.; Raethel, H. A. J. Chem., Soc., Chem. Commun. 1968, 1323.
112. (a) Liu, H. Y.; Eriks, K.; Prock, A.; Giering, W. P. Organometallics 1990, 9, 1758.
113. (b) Rahman, M. M.; Liu, H. Y.; Prock, A.; Giering, W. P. Organometallics 1987, 6, 650.
114. (a) Romeo, R.; Arena, G.; Scolaro, L. M. Inorg. Chem. 1992, 31, 4879.
115. (b) Romeo, R.; Arena, G.; Scolaro, L. M.; Plutino, M. R.; Bruno, G.; Nicolo, F. Inorg. Chem. 1994, 33, 4029.