Direct observation of C-O reductive elimination from palladium aryl alkoxide complexes to form aryl ethers

Journal of the American Chemical Society

Volumn 119, Issue 29, 1997, Pages 6787-6795

  Widenhoefer, Ross A ^a   Zhong, H Annita ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARGON; BROMINE DERIVATIVE; NITROGEN; PALLADIUM COMPLEX; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; DECOMPOSITION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; TEMPERATURE;

EID: 0030760929     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963324p     Document Type: Article

References (116)

1. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
2. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
3. (c) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
4. (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. In Poland Applications of Organotransition Metal Chemistry; University Science: Mill Valley, CA, 1987; p 322.
5. (b) Stille, J. K. In The Chemistry of the Metal-Carbon Bond, Vol. II. The Nature and Cleavage of the Metal -Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley: New York, 1985; pp 625-787.
6. (a) Kosugi, M.; Ogata, T.; Terada. M.; Sano, H.; Migita, T. Bull Chem. Soc. Jpn. 1985, 58, 3657.
7. (b) Takagi, K. Chem. Lett. 1987, 2221.
8. (c) Dickens, M. J.; Gilday, J. P.; Mowlem T. J.; Widdowson, D. A. Tetrahedron 1991, 47, 8621.
9. (d) Carpita, A.; Rossi, R.; Scamuzzi, B.; Tetrahedon Lett. 1989, 30, 2699.
10. (e) Cristau, H. J.; Chabaud, B., Chene, A.; Christol, H. Synthesis 1981, 892.
11. (a) Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927.
12. (b) Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901.
13. (c) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348.
14. (d) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133.
15. (e) Wolfe, J. P.; Rennels, R. A.; Buchwald, S L. Tetrahedron 1996, 52, 7525.
16. (f) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215.
17. (g) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217.
18. (h) Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1996, 61, 7240.
19. (i) Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969.
20. (j) Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609.
21. (a) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 4206.
22. (b) Villanueva, L. A.; Abboud, K. A.; Boncella, J. M. Organometallics 1994, 13, 3921.
23. (c) Koo, K.; Hillhouse, G. L. Organometallics 1995, 14, 4421.
24. (d) Koo, K.; Hillhouse, G. L. Organometallics 1996, 15, 2669.
25. (e) Berryhill, S. R.; Price, T.; Rosenblum, M. J. Org. Chem. 1983, 48, 158.
26. Bãranano, D.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 2937.
27. Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88, 1163.
28. After this paper was submitted, an example of aryl(C) - O reductive elimination from a palladium (aryl)tert-butoxide complex was reported by Hartwig: Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 13109.
29. Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333.
30. Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395.
31. Palucki, M.; Buchwald, S. L. Unpublished results.
32. 31P NMR spectroscopy at -52 °C.
33. obs ≈ k; the rate of decomposition of 5 generated with <1 equiv of alkoxide was not significantly different. Thermolysis of 5 in the presence of excess KBr (270 μmol/mL) or thermolysis of 5 generated from iodide precursor 2 led to no significant change in the rate or efficiency of reductive elimination. However, the effect of 1 equiv KBr on C - O reductive elimination from 5 is not known.
34. (a) Bryndza, H. E.; Calabrese, J. C.; Marsi, M.; Roe, D. C.; Tam, W.; Bercaw, J. E. J. Am. Chem. Soc. 1986, 108, 4805.
35. (b) Goldman, A. S.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 7537.
36. (c) Hoffman, D. M.; Lappas, D.; Wierda, D. A. J. Am. Chem. Soc. 1993, 115, 10538.
37. (d) Blum, O.; Mielstein, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 229.
38. (e) Bernard, K. A.; Rees, W. M.; Atwood, J. D. Organometallics 1986, 5, 390.
39. (a) Morita, D. K.; Stille, J. K.; Norton, J. R. J. Am. Chem. Soc. 1995, 117, 8576.
40. (b) Kong, K.-C; Cheng, C.-H. J. Am. Chem. Soc. 1991, 113, 6313.
41. (c) Segelstein, B. E.; Butler, T. W.; Chenard, B. L. J. Org. Chem. 1995, 60, 12.
42. (d) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933.
43. 2 is δ ∼25 [Ozawa, F.; Kubo, A.; Hayashi, T. Chem. Lett. 1992, 2177].
44. Bovey, F. A. Nuclear Magnetic Resonance Spectroscopy, 2nd ed.; Academic Press: San Diego, CA, 1988.
45. (a) Garrou, P. E. Chem. Rev. 1985, 85, 171.
46. (b) Coulson, D. R. Chem. Commun. 1968, 1530.
47. (c) Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1976, 98, 4499.
48. (d) Taylor, N. J.; Chieh, P. C.; Carty, A. J. J. Chem. Soc., Chem. Commun. 1975, 448.
49. (e) Blake, D. M.; Nyman, C. J. J. Am. Chem. Soc. 1970, 92, 5359.
50. (f) Bellon, P. L.; Ceriotti, A.; Demartin, F.; Longoni, G.; Heaton, B. T. J. Chem. Soc., Dalton Trans. 1982, 1671.
51. 4CN)Br was employed in these crossover experiments.
52. Komiya, S.; Akai, Y.; Tanaka, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1985, 4, 1130.
53. (a) Koo, K.; Hillhouse, G. L.; Rheingold, A. L. Organometallics 1995, 14, 456.
54. (b) Matsunaga, P. T.; Mavropoulos, J. C.; Hillhouse, G. L. Polyhedron 1995, 14, 175.
55. (a) Bernard, K. A.; Churchill, M. R.; Janik, T. S.; Atwood, J. D. Organometallics 1990, 9, 12.
56. (b) Komiya, S.; Tane-ichi, S.; Yamamoto, A.; Yamamoto, T. Bull. Chem. Soc. Jpn. 1980, 53, 673.
57. (c) Bryndza, H. E.; Calabrese, J. C.; Wreford, S. S. Organometallics 1984, 3, 1603.
58. (a) Cristau, H.-J.; Cesmurs, J. -R. Ind. Chem. Libr. 1995, 7, 240.
59. (b) Cramer, R.; Coulson, D. R. J. Org. Chem. 1975, 40, 2267.
60. (a) Kundu, N. G.; Pal, M.; Mahanty, J. S.; Dasgupta, S. K. J. Chem. Soc., Chem. Commun. 1992, 41.
61. (b) Stanton, S. A.; Felman, S. W.; Parkhurst, C. S.; Godleski, S. A. J. Am. Chem. Soc. 1983, 105, 1964.
62. (c) Larock, R. C.; Gou. L. Synlett 1995, 465.
63. (d) Larock, R. C.; Berrios-Peña, N. G.; Fried, C. A. J. Org. Chem. 1991, 56, 2615.
64. (e) Larock, R. C.; Berrios-Peña, N. G.; Fried, C. A. Yum, E. K.; Tu, C.; Leong, W. J. Org. Chem. 1993, 58, 4509.
65. (f) Larock, R. C.; Harrison, L. W.; Hsu, M. H. J. Org. Chem. 1984, 49, 3664.
66. (g) Larock, R. C.; Berrios-Pena, N. G.; Narayanan, K.; J. Org. Chem. 1990, 55, 3447.
67. (a) Keegstra, M. A.; Peters, T. H. A.; Brandsma, L.. Tetrahedron 1992, 48, 3633.
68. (b) Aalten, H. L.; van Koten, G.; Grove, D. M.; Kuilman, T.; Piekstra, O. G.; Hulshof, L. A.; Sheldon, R. A. Tetrahedron 1989, 45, 5565.
69. (c) Capdevielle, P.; Maumy, M. Tetrahedron Lett. 1993, 34, 1007.
70. (d) Nobel, D. J. Chem. Soc., Chem. Commun. 1993, 419.
71. (e) Pert, D. J.; Ridley, D. D. J. Chem. 1989, 42, 421.
72. (f) Whitesides, G. M.; Sadowski, J. S.; Lilburn, J. J. Am. Chem. Soc. 1974, 96, 2829.
73. (g) Lindley, J. Tetrahedron 1984, 40, 1433.
74. (h) Bacon, R. G. R.; Rennison, S. C. J. Chem. Soc. C 1969, 308.
75. (i) Bacon, R. G. R.; Rennison, S. C. J. Chem. Soc. C 1969, 312.
76. Yamamoto, A. Adv. Organomet. Chem. 1992, 34, 111.
77. Glueck, D. S.; Winslow, L. J. N.; Bergman, R. G. Organometallics 1991, 10, 1462.
78. Otsuka, S. J. Organomet. Chem. 1980, 200, 191.
79. Stang, P. J.; Kowalski, M. H. J. Am. Chem. Soc. 1989, 111, 3356.
80. Braterman, P. S.; Cross, R. J.; Young, G. B. J. Chem. Soc., Dalton Trans. 1977, 1892.
81. (a) Michelin, R. A.; Faglia, S.; Uguagliati, P. Inorg. Chem. 1983, 22, 1831.
82. (b) Abis, L.; Sen, A.; Halpern, J. J. Am. Chem. Soc. 1978, 100, 2915.
83. -, followed by attack of the alkoxide at the ipso carbon atom.
84. (a) Dockter, D. W.; Fanwick, P. E.; Kubiak, C. P. J. Am. Chem. Soc. 1996, 118, 4846.
85. (b) Bryndza, H. E.; Calabrese, J. C.; Wreford, S. S. Organometallics 1984, 3, 1603.
86. (c) Bryndza, H. E.; Kretchmar, S. A.; Tulip, T. H. J. Chem. Soc., Chem. Commun. 1985, 977.
87. (d) Michelin, R. A.; Napoli, M.; Ros, R. J. Organomet. Chem. 1979, 175, 239.
88. (e) Bennett, M. A.; Yoshida, T. J. Am. Chem. Soc. 1978, 100, 1750.
89. (f) Arnold, D. P.; Bennett, M. A.; Crisp, G. T.; Jeffery, J. C. Adv. Chem. Ser. 1982, 196, 195.
90. (g) Bennett, M. A. J. Organomet. Chem. 1986, 300, 7.
91. (h) Bennett, M. A.; Rokicki, A. Aust. J. Chem. 1985, 38, 1307.
92. (i) Appleton, T. G; Bennett, M. A. J. Organomet. Chem. 1973, 55, C88.
93. (j) Bennett, M. A. J. Mol. Catal. 1987, 41, 1.
94. (k) Bennett, M. A.; Rokicki, A. J. Organomet. Chem. 1983, 244, C31.
95. (l) Bennett, M. A.; Rokicki, A. J. Organometallics 1985, 4, 180.
96. (m) Bryndza, H. E. Organometallics 1985, 4, 1686.
97. Michelin, R. A.; Ros, R. J. Organomet. Chem. 1979, 169, C42.
98. (a) Kegley, S. E.; Schaverien, C. J.; Freudenberger, J. H.; Bergman, R. G.; Nolan, S. P.; Hoff, C. D. J. Am. Chem. Soc. 1987, 109, 6563.
99. (b) Osakada, K.; Kim, Y.-J.; Yamamoto, A. J. Organomet. Chem. 1990, 382, 303.
100. (c) Kim, Y. J.; Osakada, K.; Takenaka, A.; Yamamoto, A. J. Am. Chem. Soc. 1990, 112, 1096.
101. (d) Osakada, K.; Kim, Y. J.; Tanaka, M.; Ishiguro, S.; Yamamoto, A. Inorg. Chem. 1991, 30, 197.
102. (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.
103. Although data are limited, existing studies indicate that the rate of reductive elimination should increase with increasing steric interaction within the complex (a) Jones, W. D.; Kuykendall, V. L. Inorg. Chem. 1991, 30, 2615. (b) Brown, J. M.; Guiry, P. J. Inorg. Chim. Acta 1994, 220, 249.
104. Although data are limited, existing studies indicate that the rate of reductive elimination should increase with increasing steric interaction within the complex (a) Jones, W. D.; Kuykendall, V. L. Inorg. Chem. 1991, 30, 2615. (b) Brown, J. M.; Guiry, P. J. Inorg. Chim. Acta 1994, 220, 249.
105. para Cl = 0.23] led to slow decomposition with no detectable formation of p-neopentoxybenzonitrile: Widenhoefer, R. A.; Buchwald, S. L. Unpublished observations.
106. Presumably, the Tol-BINAP ligand of I will span equatorial and axial sites in the trigonal bipyramid with a P - M - P bond angle = 90°, close to the value of (∼92°) observed in square planar palladium - BINAP complexes [Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158]. Likewise, the palladium-bound aryl ligand is expected to occupy the second axial position in the trigonal bipyramid [Rossi, A. R.; Hoffmann, R. Inorg. Chem. 1975, 14, 365].
107. Presumably, the Tol-BINAP ligand of I will span equatorial and axial sites in the trigonal bipyramid with a P - M - P bond angle = 90°, close to the value of (∼92°) observed in square planar palladium - BINAP complexes [Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158]. Likewise, the palladium-bound aryl ligand is expected to occupy the second axial position in the trigonal bipyramid [Rossi, A. R.; Hoffmann, R. Inorg. Chem. 1975, 14, 365].
108. Komiya, S.; Abe, Y.; Yamamoto, A.; Yamamoto, T. Organometallics 1983, 2, 1466.
109. Tatsumi, K.; Nakamura, A.; Komiya, S.; Yamamoto, A.; Yamamoto, T. J. Am. Chem. Soc. 1984, 106, 8181.
110. Wax, M. J.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 7028.
111. (a) Hersh, W. H.; Bergman, R. G. J. Am. Chem. Soc. 1983, 105, 5846.
112. (b) Hembre, R. T.; Scott, C. P.; Norton, J. R. J. Org. Chem. 1987, 52, 3650.
113. (c) Chetcuti, M. J.; Chisholm M. H.; Folting, K.; Haitko, D. A.; Huffman, J. C. J. Am. Chem. Soc. 1982, 104, 2138.
114. (d) Halpern, J. Inorg. Chim. Acta 1982, 62, 31.
115. Braterman, P. S.; Cross, R. J.; Young, G. B. J. Chem. Soc., Chem. Commun. 1976, 1310.
116. International Critical Tables of Numerical Data, Physics, Chemistry, and Technology; Washburn, E. W., Ed.; McGraw-Hill: London, 1928; Vol. III, pp 29, 39, 221.