Recent fundamental studies on migratory insertion into metal-carbon bonds

Coordination Chemistry Reviews

Volumn 155, Issue , 1996, Pages 209-243

  Cavell, Kingsley J ^a  

^a UNIVERSITY OF TASMANIA   (Australia)

Author keywords

Alkenes; CO; d8 metal complexes; Intermediates and mechanism; Ligand influences; Migratory insertion

Indexed keywords

EID: 0030278562     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/s0010-8545(96)90182-4     Document Type: Article

References (131)

1. (a) A. Yamamoto, Organotransition Metal Chemistry, Wiley, New York, 1986;
2. (b) A. Mortreux and F. Petit (eds.), Industrial Applications of Homogeneous Catalysis, Reidel, Dordrecht, 1988;
3. (c) W.R. Moser and D.W. Slocum (eds.), Homogeneous Transition Metal Catalysed Reactions, American Chemical Society, Washington, 1992.
4. H.M. Colquhoun, D.J. Thompson and M.V. Twigg (eds.), Carbonylation. Direct Synthesis of Carbonyl Compounds, Plenum, New York, 1991.
5. H. Sinn and W. Kaminsky, Adv. Organomet. Chem., 18 (1980) 99; (a) W. Kaminsky, in R.P. Quirk (ed.), Transition Metal Catalysed Polymerization, Harwood Academic Publishers, New York 1983, p. 225; (c) W. Kaminsky and H. Sinn, Transition Metals and Organometallics as Catalysts for Olefin Polymerization, Springer, Berlin, 1988; (d) Makromol. Chem., Macromol. Symp., 66 (1993) 1-334; (e) P.C. Mohring and N.J. Coville, J. Organomet. Chem., 479 (1994) 1; (f) H. Hocker, R.E. Bareiss, W. Guth, B. Jung, and I. Miesel (eds.), Macromol. Symp.: Stereospecific Polymerisation (STEPOL '94), Huthig and Wepf, Zug, Switzerland, 1995; (g) H.H. Brintzinger, D. Fischer, R. Mulhaupt, B. Rieger and R. Waymouth, Angew. Chem. Int. Ed. Engl., 34 (1995) 1143.
6. (a) W. Kaminsky, in R.P. Quirk (ed.), Transition Metal Catalysed Polymerization, Harwood Academic Publishers, New York 1983, p. 225;
7. (c) W. Kaminsky and H. Sinn, Transition Metals and Organometallics as Catalysts for Olefin Polymerization, Springer, Berlin, 1988;
8. (d) Makromol. Chem., Macromol. Symp., 66 (1993) 1-334;
9. (e) P.C. Mohring and N.J. Coville, J. Organomet. Chem., 479 (1994) 1;
10. (f) H. Hocker, R.E. Bareiss, W. Guth, B. Jung, and I. Miesel (eds.), Macromol. Symp.: Stereospecific Polymerisation (STEPOL '94), Huthig and Wepf, Zug, Switzerland, 1995;
11. (g) H.H. Brintzinger, D. Fischer, R. Mulhaupt, B. Rieger and R. Waymouth, Angew. Chem. Int. Ed. Engl., 34 (1995) 1143.
12. (a) A. Sen, Chemtech, (1984) 48;
13. (b) A. Sen, Adv. Polym. Sci., 73-74 (1986) 125;
14. (c) E. Drent, Pure Appl. Chem., 62 (1990) 661;
15. (d) A. Sen, Acc. Chem. Res., 26 (1993) 303.
16. (a) S.M. Pillar, M. Ravindranathan and S. Sivaram, Chem. Rev., 86 (1986) 353;
17. (b) J. Skupinska, Chem. Rev., 91 (1991) 613;
18. (c) A.M. Al-Jarallah, J.A. Anabtawi, M.A.B. Siddiqui, A.M. Aitani and A.W. Al-Sa'doun, Catal. Today, 14 (1992) 1.
19. (a) D. Milstein, Acc. Chem. Res., 21 (1988) 428;
20. (b) E. Drent, P. Arnoldy and P.H.M. Budzelaar, J. Organomet. Chem., 455 (1993) 247.
21. E. Drent, P. Arnoldy and P.H.M. Budzelaar, J. Organomet. Chem., 475 (1994) 57.
22. (a) R.J. Mawby, F. Basolo and R.G. Pearson, J. Am. Chem. Soc., 86 (1964) 5043;
23. (b) R.J. Mawby, F. Basolo and R.G. Pearson, Inorg. Chem., 6 (1967) 2074.
24. K. Noack and F. Calderazzo, J. Organomet. Chem., 10 (1967) 101.
25. T.C. Flood, J.E. Jensen and J.A. Statler, J. Am. Chem. Soc., 103 (1981) 4410.
26. F.J. Garcia Alonso, A. Llamazares, V. Riviera, M. Vivanco, M.R. Diaz and S. Garcia Granda, J. Chem. Soc. Chem. Commun., (1991) 1058.
27. M. Pankowski and M. Bigorgne, J. Organomet. Chem., 251 (1983) 333.
28. T.C. Flood, K.D. Campbell, H.H. Downs and S. Nakanishi, Organometallics, 2 (1983) 1590.
29. H. Brunner, B. Hammer, I. Bernal and M. Draux, Organometallics, 2 (1983) 1595.
30. T.C. Flood and K.D. Campbell, J. Am. Chem. Soc., 106 (1984) 2853.
31. S.C. Wright and M.C. Baird, J. Am. Chem. Soc., 107 (1985) 6899.
32. A. Earle and C.R. Jablonski, J. Chem. Soc. Dalton Trans., (1986) 2137.
33. C. Jablonski, Organometallics, 11 (1992) 658.
34. D. Monti and M. Bassetti, J. Am. Chem. Soc., 115 (1993) 4658.
35. P.W.N.M. van Leeuwen, C.S. Roobeek and H. van der Heijden, J. Am. Chem. Soc., 116 (1994) 12117.
36. P.W.N.M. van Leeuwen and C.S. Roobeek, Rec. Trav. Chim. Pays-Bas, 114 (1995) 73.
37. P.E. Garrou and R.F. Heck, J. Am. Chem. Soc., 98 (1976) 4115.
38. E.G. Samsel and J.R. Norton, J. Am. Chem. Soc., 106 (1984) 5505.
39. K.J. Cavell and H. Jin, J. Chem. Soc. Dalton Trans., in press.
40. P.W.N.M. van Leeuwen, C.F. Roobeek and J.H.G. Frijns, Organometallics, 9 (1990) 1211.
41. R.E. Rulke, I.M. Han, C.J. Elsevier, K. Vrieze, P.W.N.M. van Leeuwen, C.F. Roobeek, M.C. Zoutberg, Y.F. Wang and C.H. Stam, Inorg. Chim. Acta, 169 (1990) 5.
42. B.A. Markies, P. Wijkens, J. Boersma, A.L. Spek and G. van Koten, Recl. Trav. Chim. Pays-Bas, 110 (1991) 133.
43. V. De Felice, M.E. Cucciolito, A. De Renzi, F. Ruffo and D. Tesauro, J. Organomet. Chem., 493 (1995) 1.
44. S.A. Macgregor, Z. Lu, O. Eisenstein and R.H. Crabtree, Inorg. Chem., 33 (1994) 3616 and references cited therein.
45. S.Y. Desjardins, K.J. Cavell, H. Jin, B.W. Skelton and A.H. White, submitted to J. Organomet. Chem.
46. M. Brookhart, A.F. Volpe, Jr., D.M. Lincoln, I.T. Horvath and J.M. Millar, J. Am. Chem. Soc., 112 (1990) 5634.
47. M. Brookhart, E. Hauptman and D.M. Lincoln, J. Am. Chem. Soc., 114 (1992) 10394.
48. F.C. Rix and M. Brookhart, J. Am. Chem. Soc., 117 (1995) 1137.
49. L.K. Johnson, C.M. Killian and M. Brookhart, J. Am. Chem. Soc., 117 (1995) 6414.
50. I. Tóth and C.J. Elsevier, J. Chem. Soc. Chem. Commun., (1993) 529.
51. H. Berke and R. Hoffmann, J. Am. Chem. Soc., 100 (1978) 7224.
52. S. Sakaki, K. Kitaura, K. Morokuma and K. Ohkubo, J. Am. Chem. Soc., 105 (1983) 2280.
53. (a) N. Koga and K. Morokuma, J. Am. Chem. Soc., 107 (1985) 7230;
54. (b) N. Koga and K. Morokuma, J. Am. Chem. Soc., 108 (1986) 6139.
55. R.J. Cross and J. Gemmill, J. Chem. Soc. Dalton Trans., (1981) 2317.??
56. (a) N. Koga, S. Obara, K. Kitaura and K. Morokuma, J. Am. Chem. Soc., 107 (1985) 7109;
57. (b) N. Koga, C. Daniel, J. Han, X.Y. Fu and K. Morokuma, J. Am. Chem. Soc., 109 (1987) 3455;
58. (c) C. Daniel, N. Koga, J. Han, X.Y. Fu and K. Morokuma, J. Am. Chem. Soc., 110 (1988) 3773;
59. (d) N. Koga, S.Q. Jin and K. Morokuma, J. Am. Chem. Soc., 110 (1988) 4317;
60. (e) N. Koga and K. Morokuma, Chem. Rev., 91 (1991) 823.
61. N. Koga and K. Morokuma, New J. Chem., 15 (1991) 749.
62. (a) A.K. Rappe, J. Am. Chem. Soc., 109 (1987) 5605;
63. (b) A. Dedieu, S. Sakaki, A. Strich and P.E.M. Siegbahn, Chem. Phys. Lett., 133 (1987) 317;
64. (c) F.U. Axe and D.S. Marynick, Chem. Phys. Lett., 141 (1987) 455;
65. (d) F.U. Axe and D.S. Marynick, J. Am. Chem. Soc., 110 (1988) 3728;
66. (e) A.L. Tchougreeff, Yu.V. Gulevich and I.A. Misurkin, J. Organomet. Chem., 455 (1993) 261.
67. M.R.A. Blomberg, C.A.M. Karlsson and P.E.M. Siegbahn, J. Phys. Chem., 97 (1993) 9341.
68. B.A. Markies, Ph. D. Thesis, Universiteit Utrecht, Utrecht, Netherlands, 1994.
69. K.E. Frankcombe, K.J. Cavell, B.F. Yates and R.B. Knott, J. Phys Chem., in press.
70. G.K. Anderson and R.J. Cross, Acc. Chem. Res., 17 (1984) 67.
71. (a) F. Calderazzo, Angew. Chem. Int. Ed. Engl., 16 (1977) 299;
72. (b) E.J. Kuhlmann and J.J. Alexander, Coord. Chem. Rev., 33 (1980) 195.
73. M. Huser, M.-T. Youinou and J.A. Osborn, Angew. Chem. Int. Ed. Engl., 28 (1989) 1386.
74. F. Ozawa, T.-I. Son, K. Osakada and A. Yamamoto, J. Chem. Soc. Chem. Commun., (1989) 1067.
75. S. Dire, R. Campostrini, G. Carturan, M. Calligaris and G. Nardin, J. Organomet. Chem., 390 (1990) 267.
76. A. Yamamoto, F. Ozawa, K. Osakada, L. Huang, T.-I. Son, N. Kawasaski and M.-K. Doh, Pure Appl. Chem., 63 (1991) 687.
77. V. Grushin and H. Alper, Organometallics, 12 (1993) 1890.
78. G.P. Chiusoli, Transition Met. Chem., 16 (1991) 553.
79. A. Yamamoto, Bull. Chem. Soc. Jpn., 68 (1995) 433.
80. G.K. Anderson and G.J. Lumetta, Organometallics, 4 (1985) 1542.
81. F. Ozawa, T. Hayashi, H. Koide and A. Yamamoto, J. Chem. Soc. Chem. Commun., (1991) 1469.
82. G.P.C.M. Decker, C.J. Elsevier, K. Vrieze and P.W.N.M. van Leeuwen, Organometallics, 11 (1992) 1598.
83. G.P.C.M. Dekker, A. Buijs, C.J. Elsevier, K. Vrieze, P.W.N.M. van Leeuwen, W.J.J. Smeets, A.L. Spek, Y.F. Wang and C.H. Stam, Organometallics., 11 (1992) 1937.
84. W. de Graaf, J. Boersma and G. van Koten, Organometallics, 9 (1990) 1479.
85. V. De Felice, V.G. Albano, C. Castellari, M.E. Cucciolito and A. De Renzi, J. Organomet. Chem., 403 (1991) 269.
86. M. Brookhart, F.C. Rix, J.M. DeSimone and J.C. Barborak, J. Am. Chem. Soc., 114 (1992) 5894.
87. R. van Asselt and C.J. Elsevier, Organometallics, 11 (1992) 1999.
88. R. van Asselt, E.E.C.G. Gielens, R.E. Rulke and C.J. Elsevier, J. Chem. Soc. Chem. Commun., (1993) 1203.
89. B.A. Markies, K.A.N. Verkerk, M.H.P. Rietveld, J. Boersma, H. Kooijman, A.L. Spek and G. van Koten, J. Chem. Soc. Chem. Commun., (1993) 1317.
90. R. van Asselt, E.E.C.G. Gielens, R.E. Rulke, K. Vrieze and C.J. Elsevier, J. Am. Chem. Soc., 116 (1994) 977.
91. B.A. Markies, D. Kruis, M.H.P. Rietveld, K.A.N. Verkerk, J. Boersma, H. Kooijman, M.T. Lakin, A.L. Spek and G. van Koten, J. Am. Chem. Soc., 117 (1995) 5263.
92. F. Gerhards, G.J.P. Britovsek and K.J. Cavell, Technisch Chemisches Fortgeschrittenenpraktikum Report der RWTH Aachen.
93. W. de Graaf, J. Boersma, D.M. Grove, A.L. Spek and G. van Koten, Recl. Trav. Chim. Pays-Bas, 107 (1988) 299.
94. P. Wehman, R.E. Rulke, V. E Kaasjager, P.C.J. Kamer, H. Kooijman, A.L. Spek, C.J. Elsevier, K. Vrieze and P.W.N.M. van Leeuwen, J. Chem. Soc. Chem. Commun., (1995) 331.
95. (a) K.J. Cavell, H. Jin, B.W. Skelton and A.H. White, J. Chem. Soc. Dalton Trans., (1992) 2923;
96. (b) K.J. Cavell, H. Jin, B.W. Skelton and A.H. White, J. Chem. Soc. Dalton Trans., (1993) 1973.
97. H. Jin and K.J. Cavell, J. Chem. Soc. Dalton Trans., (1994) 415.
98. H. Jin, K.J. Cavell, B.W. Skelton and A.H. White, J. Chem. Soc. Dalton Trans., (1995) 2159.
99. J.L. Hoare, K.J. Cavell, R. Hecker, B.W. Skelton and A.H. White, submitted to J. Chem. Soc. Dalton Trans.
100. S.Y. Desjardins, K.J. Cavell, H. Jin, B.W. Skelton and A.H. White, submitted to J. Organomet. Chem.
101. (a) D.L. Reger and D.G. Gaza, Organometallics, 12 (1993) 554;
102. (b) E. Lindner, J. Dettinger, R. Fawzi and M. Steinman, Chem. Ber., 126 (1993) 1347.
103. A.J. Paviglianiti, D.J. Min, W.C. Fultz and J.L. Burmeister, Inorg. Chim. Acta, 159 (1989) 65.
104. (a) B.L. Booth, M. Gardiner and R.N. Hazeldine, J. Chem. Soc. Dalton Trans., (1975) 1856;
105. (b) P. DeShong, D.R. Sidler, P.J. Rybczynski, G.A. Slough and A.L. Rheingold, J. Am. Chem. Soc., 110 (1988) 2575.
106. C.-S. Li, C.-H. Cheng, F.-L. Liao and S.-L. Wang, J. Chem. Soc. Chem. Commun., (1991) 710.
107. T. Hayashi, A. Kubo and F. Ozawa, Pure Appl. Chem., 64 (1992) 421.
108. M. Catellani and G.P. Chiusoli, J. Organomet. Chem., 437 (1992) 369.
109. C.-S. Li, D.-C. Jou, C.-H. Cheng, F.-L. Liao and S.-L. Wang, Organometallics, 12 (1993) 3553.
110. C.-S. Li, D.-C. Jou and C.-H. Cheng, Organometallics, 12 (1993) 3945.
111. M. Portnoy, Y. Ben-David and D. Milstein, Organometallics, 12 (1993) 4734.
112. M. Portnoy, Y. Ben-David, I. Rousso and D. Milstein, Organometallics, 13 (1994) 3465.
113. J.-P. Duan and C.-H. Cheng, Organometallics, 14 (1995) 1608.
114. (a) C. Moberg, L. Sutin and A. Heumann, Acta Chem. Scand., 45 (1991) 77;
115. (b) A.C. Aibeniz and P. Espinet, J. Organomet. Chem., 452 (1993) 229;
116. (c) M. Pfeffer, J.-P. Sutter, A. DeCian and J. Fischer, Inorg. Chim. Acta, 220 (1994) 115.
117. D. Roberto, M. Catellani and G.P. Chiusoli, Gazz. Chim. Ital., 120 (1990) 251.
118. A.C. Albeniz, P. Espinet, Y. Jeannin, M. Philoche-Levisalles and B.E. Mann, J. Am. Chem. Soc., 112 (1990) 6594.
119. W.M. Vetter and A. Sen, J. Organomet. Chem., 378 (1989) 485.
120. J.S. Brumbaugh, R.R. Whittle, M. Parvez and A. Sen, Organometallics, 9 (1990) 1735.
121. B.A. Markies, M.H.P. Rietveld, J. Boersma, A.L. Spek and G. van Koten, J. Organomet. Chem., 424 (1992) C12.
122. F. Ozawa, T. Hayashi, H. Koide and A. Yamamoto, J. Chem. Soc. Chem. Commun., (1991) 1469.
123. G.P.C.M. Decker, C.J. Elsevier, K. Vrieze, P.W.N.M. van Leeuwen and C.F. Roobeek, J. Organomet. Chem., 430 (1992) 357.
124. (a) C.-S. Li, C.-H. Cheng, S.-S. Cheng and J.-S. Shaw, J. Chem. Soc. Chem. Commun., (1990) 1774;
125. (b) W.D. McGhee and D.P. Riley, Organometallics, 11 (1992) 900.
126. (a) V.G. Albao, D. Braga, V. De Felice, A. Panunzi and A. Vitagliano, Organometallics, 6 (1987) 517;
127. (b) M.E. Cucciolito, V. De Felice, A. Panunzi and A. Vitagliano, Organometallics, 8 (1989) 1180;
128. (c) V. De Felice, A. De Renzi, D. Tesauro and A. Vitagliano, Organometallics, 11 (1992) 3669.
129. B.A. Markies, P. Wijkens, H. Kooijman, A.L. Spek, J. Boersma and G. van Koten, J. Chem. Soc., Chem. Commun., (1992) 1420.
130. (a) N. Carr, B.J. Dunne, L. Mole, A.G. Orpen and J.L. Spencer, J. Chem. Soc. Dalton Trans., (1991) 863;
131. (b) L. Mole, J.L. Spencer, N. Carr and A.G. Orpen, Organometallics, 10 (1991) 49.