Bite Angle Effects of Diphosphines in Carbonylation Reactions

Modern Carbonylation Methods

Volumn , Issue , 2008, Pages 1-25

  Van Leeuwen, Piet W N M ^a   Freixa, Zoraida ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

Bite angle effect; Diphosphines; Ligand modified Monsanto process; Modern carbonylation methods; Palladium catalyzed CO ethene copolymerization; Platinum catalyzed alkene hydroformylation; Rhodium catalyzed hydroformylation; Rhodium catalyzed methanol carbonylation

Indexed keywords

EID: 84891006526     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527621545.ch1     Document Type: Chapter

References (97)

1. Devon, T.J., Phillips, G.W., Puckette, T.A., Stavinoha, J.L. and Vanderbilt, J.J. (1987) Chelate Ligands for Low Pressure Hydroformylation Catalyst and Process Employing Same Eastman Kodak Company.
2. Kranenburg, M., van der Burgt, Y.E.M., Kamer, P.C.J. and van Leeuwen, P.W.N.M. (1995) New diphosphine ligands based on heterocyclic aromatics inducing very high regioselectivity in rhodium-catalyzed hydroformylation: effect of the bite angle. Organometallics, 14, 3081.
3. Casey, C.P. and Whiteker, G.T. (1990) The natural bite angle of chelating dipho-sphines. Israel Journal of Chemistry, 30, 299.
4. Goertz, W., Kamer, P.C.J., van Leeuwen, P. W.N.M. and Vogt, D. (1997) Application of chelating diphosphine ligands in the nickel-catalysed hydrocyanation of alk-1-enes and omega-unsaturated fatty acid esters. Journal of the Chemical Society, Chemical Communications, 1521.
5. Freixa, Z. and van Leeuwen, P.W.N.M. (2003) Bite angle effects in diphosphine metal catalysts: steric or electronic? Journal of the Chemical Society, Dalton Transactions, 1980.
6. vanLeeuwen, P.W.N.M., Kamer, P.C.J., Reek, J.N.H. and Dierkes, P. (2000) Ligand bite angle effects in metal-catalyzed C-C bond formation. Chemical Reviews, 100, 2741.
7. Kamer, P.C.J., van Leeuwen, P.W.N.M. and Reek, J.N.H. (2001) Wide bite angle diphosphines: xantphos ligands in transition metal complexes and catalysis. Accounts of Chemical Research, 34, 895.
8. Kamer, P.C.J., Reek, J.N.H. and van Leeuwen, P.W.N.M. (1998) Designing ligands with the right bite. Chemtech, 28, 27.
9. Dierkes, P. and van Leeuwen, P.W.N.M. (1999) The bite angle makes the difference: a practical parameter for diphosphine ligands. Journal of the Chemical Society, Dalton Transactions, 1519.
10. Zuidema, E., vanLeeuwen, P.W.N.M. and Bo, C. (2005) Reductive elimination of organic molecules from palladium-diphosphine complexes. Organometallics, 24, 3703.
11. Carbó, J.J., Maseras, F., Bo, C. and van Leeuwen, P.W.N.M. (2001) Unraveling the origin of regioselectivity in rhodium diphosphine catalyzed hydroformylation. A DFT QM/MM study. Journal of the American Chemical Society, 123, 7630.
12. van der Slot, S.C., Duran, J., Luten, J., Kamer, P.C.J. and van Leeuwen, P.W.N.M. (2002) Rhodium-catalyzed hydroformylation and deuterioformylation with pyrrolyl-based phosphorus amidite ligands: influence of electronic ligand properties. Organometallics, 21, 3873.
13. Pacciello, R. (2007) private communication.
14. van Rooy, A., Goubitz, K., Fraanje, J., Kamer, P.C.J., van Leeuwen, P.W.N.M., Veldman, N. and Spek, A.L. (1996) Bulkydiphosphite-modified rhodium catalysts: hydroformylation and characterization. Organometallics, 15, 835;
15. Broussard, M.E., Juma, B., Train, S.G., Peng, W.J., Laneman, S.A. and Stanley, G.G. (1993) A bimetallic hydroformylation catalyst: high regioselectivity and reactivity through homobimetallic cooperativity. Science, 260, 1784;
16. van der Veen, L.A., Kamer, P.C.J. and van Leeuwen, P.W.N.M. (1999) Hydroformylation of internal olefins to linear aldehydes with novel rhodium catalysts. Angewandte Chemie-International Edition in English, 38, 336.
17. Casey, C.P., Whiteker, G.T., Melville, M.G., Petrovich, L.M., Gavney, J.A., Jr, and Powell, D.R. (1992) Diphosphines with natural bite angles near 120° increase selectivity for n-aldehyde formation in rhodium-catalyzed hydroformylation. Journal of the American Chemical Society, 114, 5535.
18. van der Veen, L.A., Keeven, P.H., Schoemaker, G.C., Reek, J.N.H., Kamer, P.C.J., van Leeuwen, P.W.N.M., Lutz, M. and Spek, A.L. (2000) Origin of the bite angle effect on rhodium diphosphine catalyzed hydroformylation. Organometallics, 19, 872.
19. Heck, R.F. and Breslow, D.S. (1961) Reaction of cobalt hydrotetracarbonyl with olefins. Journal of the American Chemical Society, 83, 4023;
20. Heck, R.F. and Breslow, D.S. (1962) Acylcobalt carbonyls and their triphenylphosphine complexes. Journal of the American Chemical Society, 84, 2499.
21. Brown, J.M. and Kent, A.G. (1987) Structural characterisation in solution of intermediates in rhodium-catalysed hydroformylation and their interconversion pathways. Journal of the Chemical Society, Perkin Transactions 2, 1597.
22. Hughes, O.R. and Unruh, J.D. (1981) Hydroformylation catalyzed by rhodium complexes with diphosphine ligands. Journal of Molecular Catalysis, 12, 71;
23. Sanger, A.R. (1977) Hydroformylation of 1-hexene catalysed by complexes of rhodium(I) with di-or tritertiary phosphines. Journal of Molecular Catalysis, 3, 221;
24. Sanger, A.R. and Schallig, L.R. (1977) The structures and hydroformylation catalytic activities of polyphosphine complexes of rhodium(I), and related complexes immobilised on polymer supports. Journal of Molecular Catalysis, 3, 101;
25. Pittman, C.U. and Hirao, A. (1978) Hydroformylationcatalyzedby cis-chelated rhodium complexes-extension to polymer-anchored cis-chelated rhodium catalysts. The Journal of Organic Chemistry, 43, 640.
26. vanderVeen, L.A., Boele, M.D.K., Bregman, F.R., Kamer, P.C.J., van Leeuwen, P.W.N.M., Goubitz, K., Fraanje, J., Schenk, H. and Bo, C. (1998) Electronic effect on rhodium diphosphine catalyzed hydroformylation: the bite angle effect reconsidered. Journal of the American Chemical Society, 120, 11616.
27. van der Veen, L.A., Kamer, P.C.J. and van Leeuwen, P.W.N.M. (1999) New phosphacyclic diphosphines for rhodium catalyzed hydroformylation. Organometallics, 18, 4765.
28. Casey, C.P., Paulsen, E.L., Beuttenmueller, E.W., Proft, B.R., Petrovich, L.M., Matter, B. A. and Powell, D.R. (1997) Electron withdrawing substituents on equatorial and apical phosphines have opposite effects on the regioselectivity of rhodium catalyzed hydroformylation. Journal of the American Chemical Society, 119, 11817;
29. Casey, C.P., Paulsen, E.L., Beuttenmueller, E.W., Proft, B.R., Matter, B.A. and Powell, D.R. (1999) Electronically dissymmetric DIPHOS derivatives give higher n:i regioselectivity in rhodium-catalyzed hydroformylation than either of their symmetric counterparts. Journal of the American Chemical Society, 121, 63;
30. Herrmann, W.A., Kohlpaintner, C.W., Herdtweck, E. and Kiprof, P. (1991) Structure and metal coordination of the diphosphane 2,2'-bis((diphenylphosphino) methyl)-1,1'-biphenyl (BISBI). Inorganic Chemistry, 30, 4271.
31. Unruh, J.D. and Christenson, J.R. (1982) A study of the mechanism of rhodium phosphine catalyzed hydroformylation: use of 1,1'-bis(biarylphosphino) ferrocene ligands. Journal of Molecular Catalysis, 14, 19.
32. Zuidema, E., Escorihuela, L., Eichelsheim, T., Carbó, J.J., Bo, C., Kamer, P.C.J. and van Leeuwen, P.W.N.M. (2007) The rate-determining step in the rhodium-xantphos catalyzed hydroformylation of 1-octene, Chem. Eur. J. B, accepted.
33. Kawabata, Y., Hayashi, T. and Ogata, I. (1979) Platinum-diphosphine-tin systems as active and selective hydroformylation catalysts. Journal of the Chemical Society, Chemical Communications, 462.
34. Hayashi, T., Kawabata, Y, Isoyama, T. and Ogata, I. (1981) Platinum chloride-diphosphine-tin(II) halide systems as active and selective hydroformylation catalysts. Bulletin of the Chemical Society of Japan, 54, 3438;
35. Schwager, I. and Knifton, J.F. (1976) Homogeneous olefin hydroformylation catalyzed by ligand stabilized platinum(II)-group-IVb metal halide complexes. Journal of Catalysis, 45, 256;
36. 2/L catalytic system. 3. The effect of the phosphorus ligand L. Journal of Molecular Catalysis, 63, 15.
37. Tang, S.C. and Kim, L. (1982) Homogeneous hydroformylation of internal olefins by platinum tin cationic complexes. Journal of Molecular Catalysis, 14 (1), 231;
38. van Leeuwen, P.W.N.M., Roobeek, C.F., Wife, R.L. and Frijns, J.H.G. (1986) Platinum hydroformylation catalysts containing diphenylphosphine oxide ligands. Journal of the Chemical Society, Chemical Communications, (1), 31;
39. Botteghi, C., Paganelli, S., Matteoli, U., Scrivanti, A., Ciorciaro, R. and Venanzi, L.M. (1990) A new catalytic system for the hydroformylation of styrene using alkene complexes of platinum(0). Helvetica Chimica Acta, 73, 284.
40. Meessen, P., Vogt, D. and Keim, W. (1998) High regioselective hydroformylation of internal, functionalized olefins applying Pt-Sn complexes with large bite angle diphosphines. Journal of Organometallic Chemistry, 551, 165;
41. van Duren, R., Cornelissen, L.L.J.M., Van der Vlugt, J.I., Huijbers, J.P.L., Mills, A.M., Spek, A.L., Muller, C. and Vogt, D. (2006) Chiral (diphosphonite)platinum complexes in asymmetric hydroformylation. Helvetica Chimica Acta, 89, 1547.
42. Agbossou, F., Carpentier, J.F. and Mortreux, A. (1995) Asymmetric hydroformylation. Chemical Reviews, 95, 2485.
43. van der Veen, L.A., Keeven, P.K., Kamer, P.C. J. and van Leeuwen, P.W.N.M. (2000) Wide bite angle amines, arsine and phosphine ligands in rhodium and platinum/tin catalysed hydroformylation. Journal of the Chemical Society, Dalton Transactions, 2105.
44. Sen, A. and Lai, T.W. (1982) Novel palladium(II) catalyzed copolymerization of carbon monoxide with olefins. Journal of the American Chemical Society, 104, 3520;
45. Lai, T.W. and Sen, A. (1984) Palladium(II)-catalyzed copolymerization of carbon monoxide with ethylene. Direct evidence for a single mode of chain growth. Organometallics, 3, 866.
46. Drent, E. (1984) Process for the preparation of polyketones. EP 0121965 (to Shell), Chemical Abstracts, 1985, 102, 464223.
47. Drent, E., Broekhoven, J.A.M. and Doyle, M.J. (1991) Efficient palladium catalyst for the copolymerization of carbon monoxide with olefins to produce perfectly alternating polyketones. Journal of Organometallic Chemistry, 417, 235.
48. del Rio, I., Claver, C. and van Leeuwen, P.W.N.M. (2001) On the mechanism of the hydroxycarbonylation of styrene with palladium systems. European Journal of Inorganic Chemistry, (11), 2719;
49. Verspui, G., Moiseev, I.I. and Sheldon, R.A. (1999) Reaction intermediates in the Pd/tppts-catalyzed aqueous phase hydrocarboxylation of olefins monitored by NMR spectroscopy (tppts = P(C6H4-m-SO3Na)3). Journal of Organometallic Chemistry, 586 (11), 196.
50. Doherty, S., Eastham, G.R., Tooze, R.P., Scanlan, T.H., Williams, D., Elsegood, M.R.J. and Clegg, W. (1999) Palladium complexes of C2-, C3- and C4-bridged bis(phospholyl) ligands: remarkably active catalysts for the copolymerization of ethylene and carbon monoxide. Organometallics, 18, 3558.
51. Zuideveld, M.A., Kamer, P.C.J., van Leeuwen, P.W.N.M., Klusener, P.A.A., Stil, H.A. and Roobeek, C.F. (1998) Chain-transfer mechanisms of the alternating copolymerization of carbon monoxide and ethene catalyzed by palladium(II) complexes: rearrangement to highly reactive enolates. Journal of the American Chemical Society, 120, 7977.
52. van Leeuwen, P.W.N.M., Zuideveld, M.A., Swennenhuis, B.H.G., Freixa, Z., Kamer, P.C.J., Goubitz, K., Fraanje, J., Lutz, M. and Spek, A.L. (2003) Alcoholysis of acylpalladium(II) complexes relevant to the alternating copolymerization of ethene and carbon monoxide and the alkoxycarbonylation of alkenes: the importance of cis-coordinating diphosphines. Journal of the American Chemical Society, 125, 5523.
53. Mul, W.P., Dirkzwager, H., Broekhuis, A.A., Heeres, H.J., van der Linden, A.J. and Orpen, A.G. (2002) Highly active, recyclable catalyst for the manufacture of viscous, low molecular weight, CO-ethene-propene based polyketone, base component for a new class of resins. Inorganica Chimica Acta, 327, 147.
54. Bianchini, C., Lee, H.M., Meli, A., Moneti, S., Vizza, F., Fontani, M. and Zanello, P. (1999) Copolymerization of carbon monoxide with ethene catalyzed by palladium(II) complexes of 1,3-bis (diphenylphosphino)propane ligands bearing different substituents on the carbon backbone. Macromolecules, 32, 4183.
55. Bianchini, C., Lee, H.M., Meli, A., Oberhauser, W., Peruzzini, M. and Vizza, F. (2002) Ligand and solvent effects in the alternating copolymerization of carbon monoxide and olefins by palladium-diphosphine catalysis. Organometallics, 21, 16.
56. Mul, W.P., Oosterbeek, H., Beitel, G.A., Kramer, G.-J. and Drent, E. (2000) in situ monitoring of a heterogeneous palladium-based polyketone catalyst, Angewandte Chemie-International Edition, 39, 1848.
57. Dossett, S.J., Gillon, A., Orpen, A.G., Fleming, J.S., Pringle, P.G., Wass, D.F. and Jones, M.D. (2001) Steric activation of chelate catalysts: efficient polyketone catalysts based on four-membered palladium(II) diphosphine chelates. Journal of the Chemical Society, Chemical Communications, 699.
58. Drent, E. and Kragtwijk, E. (1992) Process for the carbonylation of olefin. EP 0495548 (to Shell).
59. Clegg, W., Eastham, G.R., Elsegood, M.R.J., Tooze, R.P., Wang, X.L. and Whiston, K. (1999) Highly active and selective catalysts for the production of methyl propanoate via the methoxycarbonylation of ethane. Journal of the Chemical Society, Chemical Communications, 1877;
60. Tooze, R.P., Eastham, G.R., Whiston, K. and Wang, X.L. (1996) Process for the carbonylation of ethylene and catalyst system for use therein. WO 09619434 (to ICI PCL).
61. Pugh, R.I., Drent, E. and Pringle, P.G. (2001) Tandem isomerisation-carbonylation catalysis: highly active palladium(II) catalysts for the selective methoxycarbonylation of internal alkenes to linear esters. Journal of the Chemical Society, Chemical Communications, 1476.
62. Doherty, S., Robins, E.G., Knight, J.G., Newman, C.R., Rhodes, B., Champkin, P.A. and Clegg, W. (2001) Selectivity for the methoxycarbonylation of ethylene versus CO-ethylene copolymerization with catalysts based on C-4-bridged bidentate phosphines and phospholes. Journal of Organometallic Chemistry, 640, 182.
63. Drent, E., van Kragtwijk, E. and Pello, D.H. L. (1992) Carbonylation of olefins. EP 495547 (to Shell).
64. +, R-Me, n - 1). Synthesis, characterization, and catalytic activity in ethene methoxycarbonylation. Organometallics, 21, 3637.
65. Zuideveld, M.A., Swennenhuis, B.H.G., Boele, M.D.K., Guari, Y., van Strijdonck, G.P.F., Reek, J.N.H., Kamer, P.C.J., Goubitz, K., Fraanje, J., Lutz, M., Spek, A.L. and van Leeuwen, P.W.N.M. (2002) The coordination behaviour of large natural bite angle diphosphine ligands towards methyl and 4-cyanophenylpalladium(II) complexes. Journal of the Chemical Society, Dalton Transactions, 2308;
66. Yin, J.J. and Buchwald, S.L. (2002) Pd-catalyzed intermolecular amidation of aryl halides: the discovery that xantphos can be trans-chelating in a palladium complex. Journal of the American Chemical Society, 124, 6043.
67. Pugh, R.I. and Drent, E. (2002) Methoxycarbonylation versus hydroacylation of ethene: dramatic influence of the ligand in cationic palladium catalysis. Advanced Synthesis & Catalysis, 344, 837.
68. Eastham, G.R., Heaton, B.T., Iggo, J.A., Tooze, R.P., Whyman, R. and Zacchini, S. (2000) Synthesis and spectroscopic characterisation of all the intermediates in the Pd-catalysed methoxycarbonylation of ethane. Journal of the Chemical Society, Chemical Communications, 609;
69. + (L-L = 1,2-(CH2PBu2t)2C6H4): key intermediates in the catalytic methoxycarbonylation of ethene to methylpropionate. Organometallics, 21, 1832;
70. Liu, J.K., Heaton, B.T., Iggo, J.A., Whyman, R., Bickley, J.F. and Steiner, A. (2006) The mechanism of the hydroalkoxycarbonylation of ethene and alkene-CO copolymerization catalyzed by Pd-II-diphosphine cations. Chemistry-A European Journal, 12, 4417;
71. Liu, J.K, Heaton, B.T., Iggo, J.A. and Whyman, R. (2004) The complete delineation of the initiation, propagation, and termination steps of the carbomethoxy cycle for the carboalkoxylation of ethene by Pd-diphosphane catalysts. Angewandte Chemie-International Edition in English, 43, 90.
72. Tooze, R.P., Whiston, K., Malyan, A.P., Taylor, M.J. and Wilson, N.W. (2000) Evidence for the hydride mechanism in the methoxycarbonylation of ethene catalysed by palladium-triphenylphosphine complexes. Journal of the Chemical Society, Dalton Transactions, 3441.
73. Zuidema, E., Bo, C. and van Leeuwen, P.W. N.M. (2007) Ester versus polyketone formation in the palladium-diphosphine catalyzed carbonylation of ethene. Journal of the American Chemical Society, 129, 3989.
74. Smejkal, Q., Linke, D. and Baerns, M. (2005) Energetic and economic evaluation of the production of acetic acid via ethane oxidation. Chemical Engineering and Processing, 44, 421.
75. http://www.greener-industry.org/(2007).
76. Gaemers, S. and Sunley, G.J. (2004) Carbonylation process using metal-polydentate ligands catalysis. WO 2004101487 (to BP Chemicals Limited).
77. Gaemers, S. and Sunley, G.J. (2004) Carbonylation process using metal-tridentate ligand catalysts. WO 2004101488 (to BP Chemicals Limited).
78. Moloy, K.G. and Wegman, R.W. (1989) Rhodium-catalyzed reductive carbonylation of methanol. Organometallics, 8, 2883;
79. ]2. Organometallics, 14, 2931.
80. Freixa, Z., Kamer, P.C.J., Lutz, M., Spek, A. L. and van Leeuwen, P.W.N.M. (2005) Activity of SPANphos rhodium dimers in methanol carbonylation. Angewandte Chemie-International Edition, 44, 4385.
81. Müller, C., Freixa, Z., Spek, A.L., Lutz, M., Vogt, D. and van Leeuwen, P.W.N.M. (2007) Wide bite angle diphosphines: design, synthesis and coordination properties. Organometallics, submitted.
82. Broussier, R., Laly, M., Perron, P., Gautheron, B., Nifanťev, I.E., Howard, J.A.K., Kuz'mina, L.G. and Kalck, P. (1999) Neutral and cationic 1,4-diphospha-2-rhoda-3-thia-4-ferrocenophane. Journal of Organometallic Chemistry, 587, 104;
83. Martin, H.C., James, N. H., Aitken, J., Gaunt, J.A., Adams, H. and Haynes, A. (2003) Oxidative addition of Melto a rhodium(I) N-heterocyclic carbene complex. Akinetic study. Organometallics, 22, 4451.
84. -(M = Rh, Ir). Journal of the American Chemical Society, 118, 3029;
85. Chauby, V., Daran, J.-C., Berre, C.S.-L., Malbosc, F., Kalck, P., Gonzalez, O.D., Haslam, C.E. and Haynes, A. (2002) A mechanistic investigation of oxidative addition of methyl iodide to [TpRh(CO)L]. Inorganic Chemistry, 41, 3280.
86. Forster, D. (1976) Mechanism of a rhodium-complex-catalyzed carbonylation of methanol to acetic acid. Journal of the American Chemical Society, 98, 846;
87. 2-. Journal of Organometauic Chemistry, 71, C17;
88. -: the key intermediate in rhodium catalyzed methanol carbonylation. Journal of the American Chemical Society, 113, 8567;
89. -. Journal of the American Chemical Society, 115, 4093.
90. - (M-Rh, Ir). Organometallics, 24, 3053;
91. Feliz, M., Freixa, Z., van Leeuwen, P.W.N.M. and Bo, C. (2005) Revisiting the methyl iodide oxidative addition to rhodium complexes: a DFT study of the activation parameters. Organometallics, 24, 5718;
92. Kinnunen, T. and Laasonen, K. (2001) The oxidative addition and migratory 1,1-insertion in the Monsanto and Cativa processes. A density functional study of the catalytic carbonylation of methanol. Journal of Molecular Structure: Theochem, 542, 273.
93. Thomas, C.M., Mafua, R., Therrien, B., Rusanov, E., Stoeckli-Evans, H. and Süss-Fink, G. (2002) New diphosphine ligands containing ethyleneglycol and amino alcohol spacers for the rhodium-catalyzed carbonylation of methanol. Chemistry-A European Journal, 8, 3343;
94. Thomas, C.M. and Süss-Fink, G. (2003) Ligand effects in the rhodium-catalyzed carbonylation of methanol. Coordination Chemistry Reviews, 243, 125;
95. Burger, S., Therrien, B. and Süss-Fink, G. (2005) Square-planar carbonylchlororhodium(I) complexes containing trans-spanning diphosphine ligands as catalysts for the carbonylation of methanol. Helvetica Chimica Acta, 88, 478.
96. Wells, J., Williams, G.L., Haynes, A., Freixa, Z. and van Leeuwen, P.W.N.M., unpublished results.
97. Kranenburg, M., Kamer, P.C.J., van Leeuwen, P.W.N.M., Vogt, D. and Keim, W. (1995) Effect of the bite angle of diphosphines ligands on activity and selectivity in the nickel-catalysed hydrocyanation of styrene. Journal of the Chemical Society, Chemical Communications, 2177.