The F/Ph rearrangement reaction of [(Ph3P)3RhF], the fluoride congener of Wilkinson's catalyst

Journal of the American Chemical Society

Volumn 127, Issue 43, 2005, Pages 15304-15321

  Macgregor, Stuart A ^b   Roe, D Christopher ^a   Marshall, William J ^a   Bloch, Karen M ^a   Bakhmutov, Vladimir I ^c   Grushin, Vladimir V ^a  

^a DUPONT COMPANY   (United States)

^b HERIOT WATT UNIVERSITY   (United Kingdom)

^c TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CATALYSTS; CHEMICAL BONDS; DECOMPOSITION; MATHEMATICAL MODELS; SYNTHESIS (CHEMICAL);

CYCLOMETALATED COMPLEXES; INTRAMOLECULAR PROCESSES; METALLOPHOSPHORANE; WILKINSON'S CATALYST;

REACTION KINETICS;

BENZENE; FLUORIDE; METAL COMPLEX; PHOSPHINE; PHOSPHORANE DERIVATIVE; RHODIUM;

ARTICLE; CATALYST; CHEMICAL BOND; DECOMPOSITION; KINETICS; OXIDATION; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 27544436185     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja054506z     Document Type: Article

References (150)

1. Doherty, N. M.; Hoffmann, N. W. Chem. Rev. 1991, 91, 553.
2. Holloway, J. H.; Hope, E. G. J. Fluorine Chem. 1996, 76, 209.
3. Murphy, E. F.; Murugavel, R.; Roesky, H. W. Chem. Rev. 1997, 97, 3425.
4. Clark, H. C. S.; Holloway, J. H. Adv. Inorg. Fluorides 2000, 51.
5. Mezzetti, A.; Becker, C. Helv. Chim. Acta 2002, 85, 2686
6. . Also, see: Becker, C.; Kieltsch, I.; Broggini, D.; Mezzetti, A. Inorg. Chem. 2003, 42, 8417.
7. Braun, T.; Perutz, R. N. Chem. Commun. 2002, 2749.
8. Grushin, V. V. Chem. Eur. J. 2002, 8, 1006.
9. Vaska, L.; Peone, J., Jr. J. Chem. Soc., Chem. Commun. 1971, 418.
10. Vaska, L.; Peone, J., Jr. Inorg. Synth. 1974, 15, 64.
11. Jones, C. M.; Doherty, N. M. Polyhedron 1995, 14, 81.
12. Cooper, A. C.; Caulton, K. G. Inorg. Chim. Acta 1996, 251, 41.
13. Cooper, A. C.; Huffman, J. C.; Caulton, K. G. Inorg. Chim. Acta 1998, 270, 261.
14. Dorta, R.; Egli, P.; Zuercher, F.; Togni, A. J. Am. Chem. Soc. 1997, 119, 10857.
15. Krueger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837.
16. Barthazy, P.; Togni, A.; Mezzetti, A. Organometallics 2001, 20, 3472.
17. Vicente, J.; Gil-Rubio, J.; Guerrero-Leal, J.; Bautista, D. Organometallics 2004, 23, 4871.
18. Renkema, K. B.; Werner-Zwanziger, U.; Pagel, M. D.; Caulton, K. G. J. Mol. Catal. A 2004, 224, 125.
19. Cooper, A. C.; Folting, K.; Huffmann, J. C.; Caulton, K. G. Organometallics 1997, 16, 505.
20. Lobban, J. International Patent Application WO 2003089443 A1, 2003.
21. Grushin, V. V. Angew. Chem., Int. Ed. 1998, 37, 994.
22. Poulton, J. T.; Sigalas, M. P.; Eisenstein, O.; Caulton, K. G. Inorg. Chem. 1993, 32, 5490.
23. Poulton, J. T.; Sigalas, M. P.; Folting, K.; Streib, W. E.; Eisenstein, O.; Caulton, K. G. Inorg. Chem. 1994, 33, 1476.
24. Cooper, A. C.; Bollinger, J. C.; Huffman, J. C.; Caulton, K. G. New J. Chem. 1998, 22, 473.
25. Coalter, J. N., III; Huffman, J. C.; Streib, W. E.; Caulton, K. G. Inorg. Chem. 2000, 39, 3757.
26. Huang, D.; Koren, P. R.; Folting, K.; Davidson, E. R.; Caulton, K. G. J. Am. Chem. Soc. 2000, 122, 8916.
27. Caulton, K. G. New J. Chem. 1994, 18, 25.
28. Veltheer, J. E.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1995, 117, 12478.
29. Fraser, S. L.; Antipin, M. Yu.; Khroustalyov, V. N.; Grushin, V. V. J. Am. Chem. Soc. 1997, 119, 4769.
30. Pilon, M. C.; Grushin, V. V. Organometallics 1998, 17, 1774.
31. Flemming, J. P.; Pilon, M. C.; Borbulevitch, O. Ya.; Antipin, M. Yu.; Grushin, V. V. Inorg. Chim. Acta 1998, 280, 87.
32. Marshall, W. J.; Thorn, D. L.; Grushin, V. V. Organometallics 1998, 17, 5427.
33. Grushin, V. V. Organometallics 2000, 19, 1888.
34. Grushin, V. V.; Marshall, W. J. Angew. Chem., Int. Ed. 2002, 41, 4476.
35. Marshall, W. J.; Grushin, V. V. Organometallics 2003, 22, 555.
36. Marshall, W. J.; Grushin, V. V. Organometallics 2004, 23, 3343.
37. Clark, H. C. S.; Fawcett, J.; Holloway, J. H.; Hope, E. G.; Peck, L. A.; Russell, D. R. J. Chem. Soc., Dalton Trans. 1998, 1249.
38. Tilset, M.; Fjeldahl, I.; Hamon, J.-R.; Hamon, P.; Toupet, L.; Saillard, J.-Y.; Costuas, K.; Haynes, A. J. Am. Chem. Soc. 2001, 123, 9984.
39. Tilset, M.; Hamon, J.-R.; Hamon, P. Chem. Commun. 1998, 765.
40. (a) Cronin, L.; Higgitt, C. L.; Karch, R.; Perutz, R. N. Organometallics 1997, 16, 4920.
41. (b) Braun, T.; Parsons, S.; Perutz, R. N.; Voith, M. Organometallics 1999, 18, 1710.
42. Jasim, N. A.; Perutz, R. N.; Foxon, S. P.; Walton, P. H. J. Chem. Soc., Dalton Trans. 2001, 1676.
43. Jasim, N. A.; Perutz, R. N.; Archibald, S. J. Dalton Trans. 2003, 2184.
44. Reinhold, M.; McGrady, J. E.; Perutz, R. N. J. Am. Chem. Soc. 2004, 126, 5268.
45. Gil-Rubio, J.; Weberndorfer, B.; Werner, H. J. Chem. Soc., Dalton Trans. 1999, 1437.
46. Moigno, D.; Callejas-Gaspar, B.; Gil-Rubio, J.; Werner, H.; Kiefer, W. J. Organomet. Chem. 2002, 661, 181.
47. Gorol, M.; Moesch-Zanetti, N. C.; Roesky, H. W.; Noltemeyer, M.; Schmidt, H.-G. Eur. J. Inorg. Chem. 2004, 2678.
48. Barthazy, P.; Hintermann, L.; Stoop, R. M.; Worle, M.; Mezzetti, A.; Togni, A. Helv. Chim. Acta 1999, 82, 2448.
49. Barthazy, P.; Stoop, R. M.; Woerle, M.; Togni, A.; Mezzetti, A. Organometallics 2000, 19, 2844.
50. Barthazy, P.; Broggini, D.; Mezzetti, A. Can. J. Chem. 2001, 79, 904.
51. Kirkham, M. S.; Mahon, M. F.; Whittlesey, M. K. Chem. Commun. 2001, 813.
52. Braun, T.; Noveski, D.; Neumann, B.; Stammler, H.-G. Angew. Chem., Int. Ed. 2002, 41, 2745.
53. Noveski, D.; Braun, T.; Schulte, M.; Neumann, B.; Stammler, H.-G. Dalton Trans. 2003, 4075.
54. Noveski, D.; Braun, T.; Kruckemeier, S. J. Fluorine Chem. 2004, 125, 959.
55. Nilsson, P.; Plamper, F.; Wendt, O. F. Organometallics 2003, 22, 5235.
56. (a) Yahav, A.; Goldberg, I.; Vigalok, A. J. Am. Chem. Soc. 2003, 125, 13634.
57. (b) Yahav, A.; Goldberg, I.; Vigalok, A. Inorg. Chem. 2005, 44, 1547.
58. Vicente, J.; Gil-Rubio, J.; Bautista, D.; Sironi, A.; Masciocchi, N. Inorg. Chem. 2004, 43, 5665.
59. Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2004, 126, 3068.
60. Jardine, F. H. Prog. Inorg. Chem. 1981, 28, 63.
61. (a) For reviews, see: Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94,1047;
62. Top. Organomet. Chem. 1999, 3, 193.
63. (b) For the earliest original contributions to Pd/dippp-catalyzed reactions of nonactivated chloroarenes from Milstein's group, see: Ben-David, Y.; Portnoy, M.; Milstein, D. J. Am. Chem. Soc. 1989, 111, 8742;
64. J. Chem. Soc., Chem. Commun. 1989, 1816. For a full citation of Milstein's catalytic Ar-Cl activation work, see ref 55a.
65. 3P/Pd-catalyzed reactions of chlorobenzene from Osborn's group, see: Huser, M.; Youinou, M. T.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1989, 28, 1386. For a full citation of Osborn's catalytic Ar-Cl activation work, see ref 55a.
66. (d) For early work on Ar-Cl activation, catalyzed by Rh complexes of bulky, basic phosphines, see: Grushin, V. V.; Alper, H. Organometallics 1991, 10, 1620.
67. 3P-Pd catalytic system for chloroarene activation, see: Nishiyama, M.; Koie, Y. Eur. Pat. Appl. EP 802173 A1, 1997.
68. 55f
69. (f) For a review, see: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
70. Mori, K.; Mizoroki, T.; Ozaki, T. Bull. Chem. Soc. Jpn. 1976, 49, 758.
71. Ishiyama, T.; Hartwig, J. J. Am. Chem. Soc. 2000, 122, 12043.
72. Keim, W. J. Organomet. Chem. 1968, 14, 179.
73. Semmelhack, M. F.; Ryono, L. Tetrahedron Lett. 1973, 14, 2967.
74. Van Gaal, H. L. M.; Van den Bekerom, F. L. A.; Verlaan, J. P. J. J. Organomet. Chem. 1976, 114, C35.
75. Uson, R.; Oro, L. A.; Cabeza, J. A. Inorg. Synth. 1985, 23, 126.
76. McClinton, M. A. Aldrichimica Acta 1995, 28, 31.
77. Haufe, G. J. Prakt. Chem. 1996, 338, 99.
78. Grushin, V. V.; Kuznetsov, V. F.; Bensimone, C.; Alper, H. Organometallics 1995, 14, 3927.
79. Bennett, M. J.; Donaldson, P. B. Inorg. Chem. 1977, 16, 655.
80. (a) Brown, C.; Murray, M.; Schmutzler, R. J. Chem. Soc. C 1970, 878.
81. (b) Riesel, L.; Haenel, J.; Ohms, G. J. Fluorine Chem. 1988, 38, 335.
82. Kuznetsov, V. F.; Yap, G. P. A.; Bensimon, C.; Alper, H. Inorg. Chim. Acta 1998, 280, 172.
83. For a review, see: Dias, P. B.; Minas de Piedade, M. E.; Martinho Simões, J. A. Coord. Chem. Rev. 1994, 135/136, 737.
84. (a) Moloy, K. G.; Petersen, J. L. J. Am. Chem. Soc. 1995, 117, 7696.
85. (b) Huang, J.; Haar, C. M.; Nolan, S. P.; Marshall, W. J.; Moloy, K. G. J. Am. Chem. Soc. 1998, 120, 7806.
86. Mayer, J. M. Comments Inorg. Chem. 1988, 8, 125.
87. Coulson, D. R. J. Am. Chem. Soc. 1976, 98, 3111.
88. Roesky, H. W.; Sotoodeh, M.; Xu, Y. M.; Schrumpf, F.; Noltemeyer, M. Z. Anorg. Allg. Chem. 1990, 580, 131.
89. Hintermann, S.; Pregosin, P. S.; Rüegger, H. J. Organomet. Chem. 1992, 435, 225.
90. Whittlesey, M. K.; Perutz, R. N.; Greener, B.; Moore, M. H. Chem. Commun. 1997, 187.
91. Murphy, V. J.; Hascall, T.; Chen, J. Y.; Parkin, G. J. Am. Chem. Soc. 1996, 118, 7428.
92. Murphy, V. J.; Rabinovich, D.; Hascall, T.; Klooster, W. T.; Koetzle, T. F.; Parkin, G. J. Am. Chem. Soc. 1998, 120, 4372.
93. Holzbock, J.; Sawodny, W.; Walz, L. Z. Kristallogr. 1997, 212, 115.
94. Bentrup, U.; Harms, K.; Massa, W.; Pebler, J. Solid State Sci. 2000, 2, 373.
95. Braun, T.; Foxon, S. P.; Perutz, R. N.; Walton, P. H. Angew. Chem., Int. Ed. 1999, 38, 3326.
96. Jasim, N. A.; Perutz, R. N. J. Am. Chem. Soc. 2000, 122, 8685.
97. Roe, D. C.; Marshall, W. J.; Davidson, F.; Soper, P. D.; Grushin, V. V. Organometallics 2000, 19, 4575.
98. Archibald, S. J.; Braun, T.; Gaunt, J. A.; Hobson, J. E.; Perutz, R. N. Dalton Trans. 2000, 2013.
99. Brammer, L.; Bruton, E. A.; Sherwood, P. Cryst. Growth Des. 2001, 1, 277.
100. 34 using the Cambridge Mercury program, version 1.3. This is mentioned as a cautionary note that clicking on "Short Contact < (sum of vdw radii)" does not include intramolecular contacts unless they are more explicitly defined using the sub-menu "Define short contacts".
101. 6, were studied by single-crystal X-ray diffraction.
102. Cox, B. G. Modern Liquid-Phase Kinetics; Oxford University Press: Oxford, UK, 1994.
103. Lide, D. R. Handbook of Organic Solvents; CRC Press: Boca Raton, FL, 1995.
104. Gutmann, V. Electrochim. Acta 1976, 21, 661.
105. For a review of metallophosphoranes, see: Nakazawa, H.; Kubo, K.; Miyoshi, K. Bull. Chem. Soc. Jpn. 2001, 74, 2255.
106. Mason, M. R.; Verkade, J. G. Organometallics 1992, 11, 2212.
107. Macgregor, S. A.; Neave, G. W. Organometallics 2004, 23, 891.
108. Kajiyama, K.; Nakamoto, A.; Miyazawa, S.; Miyamoto, T. K. Chem. Lett. 2003, 32, 332.
109. Ortiz, J. V.; Havias, Z.; Hoffmann, R. Helv. Chim. Acta 1984, 67, 1.
110. 2Ph ligand has a highly distorted geometry and so omits the reorganization energy associated with this distortion.
111. I4-cis-5′ prior to this correction.
112. Riehl, J.-F.; Jean, Y.; Eisenstein, O.; Pélissier, M. Organometallics 1992, 11, 729.
113. 2-(P-O) phosphoranides with group 9 metals, see: (a) Toyota, K.; Yamamoto, Y.; Akiba, K.-Y. J. Organomet. Chem. 1990, 586, 171.
114. (b) De Meester, P.; Lattman, M.; Chu, S. S. C. Acta Crystallogr., Sect. C 1987 43, 162.
115. Goodman, J.; Macgregor, S. A., unpublished results.
116. Blum, O.; Frolow, F.; Milstein, D. J. Chem. Soc., Chem. Commun. 1991, 258.
117. (a) den Reijer, C. J.; Woerle, M.; Pregosin, P. S. Organometallics 2000, 19, 309.
118. (b) den Reijer, C. J.; Dotta, P.; Pregosin, P. S.; Albinati, A. Can. J. Chem. 2001, 79, 693.
119. (c) Geldbach, T. J.; Pregosin, P. S. Eur. J. Inorg. Chem. 2002, 1907.
120. Jasim, N. A.; Perutz, R. N.; Whitwood, A. C.; Braun, T.; Izundu, J.; Neumann, B.; Rothfeld, S.; Stammler, H.-G. Organometallics 2004, 23, 6140.
121. 2F bond in cis-5′.
122. Bedford, A. F.; Mortimer, C. T. J. Chem. Soc. 1960, 1622.
123. Neale, E.; Williams, L. T. D.; Moores, V. T. J. Chem. Soc. 1956, 422.
124. Brown, T. L.; LeMay, H. E., Jr.; Bursten, B. E. Chemistry: The Central Science, 7th ed.; Prentice Hall: Upper Saddle River, NJ, 1997.
125. Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1976, 98, 4499.
126. 2O (1 mol % to [Rh]) affected significantly the reaction of 1 at 60 °C. No substantial effect of CsF (22 equiv) was observed on conversion of 5 to 1 at the same temperature (60 °C) after 20, 50, and 90 min. We conclude therefore that, under our conditions, acid catalysis is unlikely to be the main channel for the F/Ph rearrangement.
127. 3RhCl]: Halpern, J.; Wong, C. S. J. Chem. Soc., Chem. Commun. 1973, 629.
128. 2Pd]: Fauvarque, J.-F.; Pflüger, F.; Troupel, M. J. Organomet. Chem. 1981, 208, 419.
129. Lewin, M.; Aizenshtat, Z.; Blum, J. J. Organomet. Chem. 1980, 184, 255.
130. Garrou, P. E. Chem. Rev. 1985, 85, 171.
131. Dahlenburg, L. J. Organomet. Chem. 1983, 251, 347.
132. Bennett, M. A.; Bhargava, S. K.; Ke, M.; Willis, A. C. Dalton Trans. 2000, 3537.
133. For a review, see: Cavell, K. J. Coord. Chem. Rev. 1996, 155, 209.
134. Hoffmann, R.; Howell, J. M.; Muetterties, E. L. J. Am. Chem. Soc. 1972, 94, 3047.
135. (a) Kong, K.-C; Cheng, C.-H. J. Am. Chem. Soc. 1991, 113, 6313.
136. (b) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441.
137. Morita, D. K.; Stille, J. K.; Norton, J. R. J. Am. Chem. Soc. 1995, 117, 8576.
138. Fóa, M.; Cassar, L. J. Chem. Soc., Dalton Trans. 1975, 2572.
139. For a recent overview of such reactions, see section 2.2 in: Grushin, V. V. Chem. Rev. 2004, 104, 1629.
140. 3PO, see: Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314;
141. J. Organomet. Chem. 1999, 576, 254.
142. Gonzalez-Carrera, V.; Goodman, J.; Macgregor, S. A., unpublished results.
143. Grushin, V. V.; Alper, H. Organometallics 1993, 12, 1890.
144. Grushin, V. V.; Bensimon, C.; Alper, H. Inorg. Chem. 1994, 33, 4804.
145. Fornies, J.; Green, M.; Spencer, J. L.; Stone, F. G. A. J. Chem. Soc., Dalton Trans. 1977, 1006.
146. Walther, D.; Heubach, K.; Böttcher, L.; Schreer, H.; Görls, H. Z. Anorg. Allg. Chem. 2002, 628, 20.
147. Green, L. M.; Meek, D. W. Organometallics 1989, 8, 659.
148. Bennett, M. A.; Latten, J. L. Inorg. Synth. 1989, 26, 200.
149. Our initial kinetic studies were carried out with samples placed in both 5-mm and 10-mm NMR tubes, with and without inert Teflon liners. These variations in the nature of the surface (glass vs Teflon) and in the glass surface-to-volume ratio did not cause an observable change in reaction rates.
150. Pimblett, G.; Garner, C. D.; Clegg, W. J. Chem. Soc., Dalton Trans. 1985, 1977.