Diphenylphosphino(phenyl pyridin-2-yl methylene)amine palladium(II) complexes: Chemoselective alkene hydrocarboxylation initiators

Journal of Organometallic Chemistry

Volumn 690, Issue 23, 2005, Pages 5264-5281

  Dyer, Philip W ^a,b   Fawcett, John ^b   Hanton, Martin J ^b,c  

^a DURHAM UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF LEICESTER   (United Kingdom)

^c SASOL TECHNOLOGY PTY LTD   (South Africa)

Author keywords

Hydrocarboxylation; P N ligands; Palladium; Polyketone

Indexed keywords

CARBOXYLATION; CATALYSIS; COMPLEXATION; KETONES; OLEFINS; PALLADIUM COMPOUNDS; PHENOLS; POLYMERS; REACTION KINETICS; X RAY CRYSTALLOGRAPHY;

HYDROCARBOXYLATION; NEUTRAL COMPLEXES; P-N LIGANDS; POLYKETONES;

AMINES;

EID: 27644485079     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2005.04.032     Document Type: Article

References (94)

1. P. Braunstein, and F. Naud Angew. Chem. Int. Ed. 40 2001 680
2. P.J. Guiry, and C.P. Saunders Adv. Synth. Catal. 346 2004 497
3. W.J. Drury III, N. Zimmermann, M. Keenan, M. Hayashi, S. Kaiser, R. Goddard, and A. Pfaltz Angew. Chem. Int. Ed. Engl. 43 2004 70
4. F. Leca, C. Lescop, and R. Réau Organometallics 23 2004 6191
5. C. Bianchini, and A. Meli Coord. Chem. Rev. 225 2002 35
6. P. Espinet, and K. Soulantica Coord. Chem. Rev. 193-195 1999 499
7. D.J. Cole-Hamilton, and R.A.M. Robertson A. Sen Catalytic synthesis of alkene-carbon monoxide copolymers and cooligomers 2003 Kluwer Academic Publishers Dordrecht 37 82 (Chapter 3)
8. R.A.M. Robertson, and D.J. Cole-Hamilton Coord. Chem. Rev. 225 2002 67
9. M. Beller, and A.M. Tafesh B. Cornils W.A. Herrmann Applied homogeneous catalysis with organometallic compounds 2002 Wiley-VCH Weinheim 182 194
10. D. Milstein Acc. Chem. Rev. 21 1988 428
11. A. Baceiredo, G. Bertrand, P.W. Dyer, J. Fawcett, N. Griep-Raming, O. Guerret, M.J. Hanton, and A.-M. Williamson New J. Chem. 25 2001 591
12. F. Dahan, P.W. Dyer, M.J. Hanton, M. Jones, D.M.P. Mingos, A.J.P. White, D.J. Williams, and A.-M. Williamson Eur. J. Inorg. Chem. 2002 732
13. P.W. Dyer, J. Fawcett, M.J. Hanton, R.D.W. Kemmitt, R. Padda, D.R. Russell, and N. Singh J. Chem. Soc. Dalton Trans. 2003 104
14. M.L. Clarke, G.L. Holliday, A.M.Z. Slawin, and J.D. Woollins J. Chem. Soc., Dalton Trans 2002 1093
15. M. Rodriguez i Zubiri, and J.D. Woollins Comm. Inorg. Chem. 24 2003 189
16. M. Brookhart, S.D. Ittel, and L.K. Johnson Chem. Rev. 100 2000 1169
17. second ed. B. Cornils W.A. Herrmann Applied homogeneous catalysis with organometallic compounds vol. 1 2002 Wiley-VCH Weinheim (Chapters 2.1, 2.2 and 2.3)
18. K.R. Reddy, K. Surekha, G.-H. Lee, S.-H. Peng, J.-T. Chen, and S.-T. Liu Organometallics 20 2001 1292
19. S.M. Aucott, A.M.Z. Slawin, and J.D. Woollins J. Organomet. Chem. 582 1999 83
20. L. Canovese, G. Chessa, L. Maini, M. Polito, C. Santo, P. Uguagliati, and F. Visentin J. Chem. Soc., Dalton Trans. 2002 3696
21. I. Fleming, and D.H. Williams Spectroscopic methods in organic chemistry fourth ed. 1987 McGraw Hill London p. 91-92
22. N.G. Anderson, and B.A. Keay Chem. Rev. 101 2001 997
23. C. Glidewell, and E.J. Leslie J.C.S. Dalton Trans. 1977 527
24. D.W. Allen, and B.F. Taylor J. Chem. Res. S 1981 220
25. R.D. Kroshefsky, R. Weiss, and J.G. Verkade Inorg. Chem. 18 1979 469
26. D.W. Allen, and B.R. Taylor J. Chem. Soc. Dalton Trans. 1982 51
27. R.G. Pearson Inorg. Chem. 12 1973 712
28. M.P. Anderson, A.L. Casalnuovo, B.J. Johnson, B.M. Mattson, A.M. Mueting, and L.H. Pignolet Inorg. Chem. 27 1988 1649
29. Y. Arikawa, M. Hidai, Y. Nishibayashi, K. Ohe, K. Segawa, and S. Uemura J. Organomet. Chem. 545 1997 381
30. A.D. Burrows, M.F. Mahon, and M. Varrone Dalton Trans. 2003 4718
31. S. Vastag, B. Heil, and L. Markü J. Mol. Catal. 5 1979 189
32. P.H.M. Budzelaar, and E. Drent Chem. Rev. 96 1996 663
33. S.M. Aucott, A.M.Z. Slawin, and J.D. Woollins J. Chem. Soc. Dalton Trans. 2001 2279
34. C.J. Cobley, and P.G. Pringle Inorg. Chim. Acta 265 1997 107
35. G.P.C.M. Dekker, C.J. Elsevier, P.W.N.M. van Leeuwen, and K. Vrieze Organometallics 11 1992 1598
36. J. Boersma, W. de Graaf, G. van Koten, W.J.J. Smeets, and A.L. Spek Organometallics 8 1989 2907
37. J. Boersma, W. de Graaf, S. Harder, J.A. Kanters, and G. van Koten J. Organomet. Chem. 358 1988 545
38. G.J. Palenik, and W.L. Steffen Inorg. Chem. 15 1976 2432
39. P-N single bond lengths: 1.77 Å, in: N.N. Greenwood, A. Earnshaw, Chemistry of the Elements, 1st ed., Butterworth Heinemann, Oxford, 1984, p. 620;
40. 1.8 Å, in: A.L. Pauling, Nature of the Chemical Bond, Cornell University Press, New York, 1960;
41. 1.76 Å: in V. Schomaker and D.P. Stevenson, J. Am. Chem. Soc. 63 (1941) 37.
42. J. March Advanced organic chemistry fourth ed. 1992 Wiley-Interscience New York p. 21
43. 13C NMR of transition metal phosphine complexes 1979 Springer-Verlag New York 114
44. H. Kobayashi, H. Nishida, T. Sonoda, N. Takada, and M. Yoshimura Bull. Chem. Soc. Jpn. 57 1984 2600
45. G.J.P. Britovsek, V.C. Gibson, and D.F. Wass Angew. Chem. Int. Ed. 38 1999 428
46. M. Brookhart, B. Grant, and A.F. Volpe Organometallics 11 1992 3920
47. C.-L. Chen, J.-T. Chen, S.-T. Liu, Y.-H. Liu, S.-M. Peng, and K.R. Reddy Organometallics 18 1999 2574
48. A. Buijs, G.P.C.M. Dekker, C.J. Elsevier, P.W.N.M. van Leeuwen, W.J.J. Smeets, A.L. Spek, C.H. Stam, K. Vrieze, and Y.F. Wang Organometallics 11 1992 1937
49. L.D. Durfee, and I.P. Rothwell Chem. Rev. 88 1988 1059
50. J.J. Alexander, and E.J. Kuhlmann Coord. Chem. Rev. 33 1980 195
51. R.E. Rülke, J.G.P. Delis, A.M. Groot, C.J. Elsevier, P.W.N.M. van Leeuwen, K. Vrieze, K. Goubitz, and H. Schenk J. Organomet. Chem. 508 1996 109
52. P.H.P. Brinkman, and G.A. Luinstra J. Organomet. Chem. 572 1999 193
53. A. Sommazzi, and F. Garbassi Prog. Polym. Sci. 22 1997 1547
54. P. Braunstein, C. Frison, and X. Morise Angew. Chem. Int. Ed. 39 2000 2867
55. J. Boersma, H. Kooijman, G. van Koten, D. Kruis, M. Lakin, B.A. Markies, M.H.P. Rietveld, A.L. Spek, and K.A.N. Verkerk J. Am. Chem. Soc. 117 1995 5263
56. J. Brumbaugh, M. Parvez, A. Sen, and R.R. Whittle Organometallics 9 1990 1735
57. J.S. Brumbaugh, and A. Sen J. Am. Chem. Soc. 110 1988 803
58. C. Bianchini, A. Meli, and W. Oberhauser Dalton Trans. 2003 2627
59. J.P. Collman, R.G. Finke, L.S. Hegedus, and J.R. Norton Principles and applications of organotransition metal chemistry 1987 University Science Books Mill Valley, CA p. 377-378
60. C. Elschenbroich, and A. Salzer Organometallics - a concise introduction second ed. 1992 VCH Weinheim p. 240-241
61. P.G. Aubel, J.G.P. Delis, P.W.N.M. van Leeuwen, A.L. Spek, N. Veldman, and K. Vrieze J. Chem. Soc., Chem. Commun. 1995 2233
62. P.G. Aubel, J.G.P. Delis, P.W.N.M. van Leeuwen, F.J.R. van Neer, A.L. Spek, N. Veldman, and K. Vrieze Organometallics 16 1997 2948
63. D.G. Cooper, and J. Powell Can. J. Chem. 51 1973 1634
64. J.H. Nelson, and D.A. Redfield Inorg. Chem. 12 1973 15
65. B. Milani, A. Scarel, G. Mestroni, S. Gladiali, R. Taras, C. Carfagna, and L. Mosca Organometallics 21 2002 4965
66. C. Carfagna, S. Gladiali, G. Mestroni, B. Milani, L. Mosca, A. Scarel, and R. Taras Organometallics 21 2002 1323
67. 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
68. C.S. Schultz, J. Ledford, J.M. DeSimone, and M. Brookhart J. Am. Chem. Soc. 122 2000 6351
69. C. Bianchini, A. Meli, G. Müller, W. Oberhauser, and E. Passaglia Organometallics 21 2002 4965
70. P. Champkin, W. Clegg, S. Doherty, M.R.J. Elsegood, G.R. Eastham, A. Harriamn, J.G. Knight, M. Betham, E.G. Robins, and R.P. Tooze Organometallics 19 2000 4957
71. K.S. Coleman, A.R. Cowley, M.L.H. Green, S.I. Pascu, N.H. Rees, and L.H. Rees J. Chem. Soc., Dalton Trans. 2001 3384
72. P. Braunstein, M.D. Fryzuk, M. Le Dall, F. Naud, S.J. Rettig, and F. Speiser J. Chem. Soc. Dalton Trans. 2000 1067
73. J.-T. Chen, G.-H. Lee, S.-T. Liu, S.-M. Peng, K.R. Reddy, K. Surekha, and W.-W. Tsai J. Chem. Soc., Dalton Trans. 2002 1776
74. E.K. van den Beuken, W.J.J. Smeets, A.L. Spek, and B.L. Feringa Chem. Commun. 1998 223
75. P.H.P. Brinkman, and G.A. Luinstra Organometallics 17 1998 5160
76. P.W.N.M. van Leeuwen, M.A. Zuideveld, B.H.G. Swennenhuis, Z. Freixa, P.C.J. Kamer, K. Goubitz, J. Fraanje, M. Lutz, and A.L. Spek J. Am. Chem. Soc. 125 2003 5523
77. G. Cavinato, and L. Toniolo J. Organomet. Chem. 398 1990 187
78. W.P. Mul, A.W. van der Made, A.A. Smaardijk, and E. Drent A. Sen Drent in catalytic synthesis of alkene-carbon monoxide copolymers and cooligomers 2003 Kluwer Academic Publishers Dordrecht 77 140 Ch. 4
79. Z. Freixa, and P.W.N.M. van Leeuwen Dalton Trans. 2003 1890
80. P.W.N.M. van Leeuwen A. Sen Catalytic synthesis of alkene-carbon monoxide copolymers and cooligomers 2003 Kluwer Academic Publishers Dordrecht 77 173 184
81. W. Clegg, G.R. Eastham, M.R.J. Elsegood, R.P. Tooze, X.L. Wang, and K. Whiston Chem. Commun. 1999 1877
82. E. Drent, J.A.M. Vanbroekhoven, and M.J. Doyle J. Organomet. Chem. 417 1991 235
83. D.J. Darensbourg, and R.L. Kump Inorg. Chem. 17 1978 2680
84. J.A. McCleverty, and G. Wilkinson Inorg. Synth. 8 1966 211
85. S. Komiya Synthesis of organometallic compounds - a practical guide 1998 Wiley-Interscience New York p. 285
86. C.J. Elsevier, J.M. Ernsting, P.W.N.M. van Leeuwen, R.E. Rulke, A.L. Spek, and K. Vrieze Inorg. Chem. 32 1993 5769
87. J. Boersma, W. de Graaf, D. Grove, G. van Koten, and A.L. Spek Rec. Trav. Chim. Pays Bas 107 1988 299
88. J.X. McDermott, J.F. White, and G.M. Whitesides J. Am. Chem. Soc. 98 1976 6521
89. G.P.C. Dekker, A. Buijs, C.J. Elsevier, P.W.N.M. van Leeuwen, W.J.J. Smeets, A.L. Spek, C.J. Stam, K. Vrieze, and Y.F. Wang Organometallics 11 1992 1937
90. E. Costa, P.G. Pringle, and M. Ravetz Inorg. Synth. 31 1997 284
91. H. Kobayashi, H. Nishida, T. Sonoda, N. Takada, and M. Yoshimura Bull. Chem. Soc. Jpn. 57 1984 2600
92. Bruker SMART (v 5.622, 2001) and SAINT-Plus (v 6.02, 1999), Bruker AXS Inc., Madison, WI, USA.
93. G.M. Sheldrick shelxtl (v 6.1, 2000) 2000 Bruker AXS Inc. Madison, WI, USA
94. G.M. Sheldrick sadabs, Program for the empirical absorption correction of area detector data 1996 University of Göttingen Germany