Palladium Complexes with Bulky Diphosphine Ligands as Highly Selective Catalysts for the Synthesis of (Bio-) Adipic Acid from Pentenoic Acid Mixtures.

Organometallics

Volumn 34, Issue 17, 2015, Pages 4281-4292

  Low, Choon Heng ^a   Nobbs, James D ^a   Van Meurs, Martin ^a   Stubbs, Ludger P ^a   Drent, Eite ^b   Aitipamula, Srinivasulu ^a   Pung, Michelle H L ^a  

^a INSTITUTE OF CHEMICAL AND ENGINEERING SCIENCES   (Singapore)

^b LEIDEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; CHELATION; ISOMERS; LIGANDS; MIXTURES; PHOSPHORUS COMPOUNDS; SINGLE CRYSTALS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

DIPHOSPHINE LIGAND; HIGH SELECTIVITY; HYDROXYCARBONYLATION; PALLADIUM COMPLEXES; SELECTIVE CATALYSTS; SINGLE CRYSTAL X-RAY DIFFRACTION; SOLID-STATE STRUCTURES; SQUARE-PLANAR COORDINATION GEOMETRY;

PALLADIUM COMPOUNDS;

EID: 84941578389     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/acs.organomet.5b00517     Document Type: Article

References (64)

1. Picataggio, S.; Beardslee, T. (Verdezyne Inc.) Biological Methods for Preparing Adipic Acid, US 20120021474, 2012,.
2. Van de Vyver, S.; Roman-Leshkov, Y. Catal. Sci. Technol. 2013, 3, 1465-1479 10.1039/C3CY20728E
3. Boussie, T. R.; Dias, E. L.; Fresco, Z. M.; Murphy, V. J.; Shoemaker, J.; Archer, R.; Jiang, H. (Rennovia Inc.) Production of Adipic Acid and Derivatives from Carbohydrate-containing Materials, US 20100317823 A1, 2010.
4. Lange, J.-P.; Vestering, J. Z.; Haan, R. J. Chem. Commun. 2007, 3488-3490 10.1039/b705782b
5. Vries, J. G. D.; Sereinig, N.; Voondervoort, E. W. M. V. d.; Jannsen, M. C. C. (DSM) Process for the Preparation of Alkanoic Acid Esters in a Carbonylation Process using Palladium Bidentate Biphosphate Ligands, WO 2012131027A1, 2012.
6. Vries, J. G. D.; Sereinig, N.; Voondervoort, E. W. M. V. d.; Jannsen, M. C. C. (DSM) Process to Produce Adipic Acid and Diesters Thereof in a Carbonylation Process using Palladium Bidentate Biphosphate Ligands, WO2012131028A1, 2012.
7. Coudray, L.; Bui, V.; Frost, J. W. (Amyris) Process for Preparing Caprolactam and Polyamides therefrom, WO 2012141997A1, 2012.
8. Wong, P. K.; Li, C.; Stubbs, L.; van Meurs, M.; Anak Kumbang, D. G.; Lim, S. C. Y.; Drent, E. (A∗STAR) Synthesis of Diacids, WO 2012134397, 2012.
9. Drent, E.; Kragtwijk, E. (Shell) Process for the Carbonylation of Olefins, EP 0495548 A2, 1992.
10. Tooze, R. P.; Eastham, G. R.; Whiston, K.; Wang, X. L. (ICI) Process for the Carbonylation of Ethylene and Catalyst System for use Therein, WO 9619434 A1, 1996.
11. Pearson, J. M.; Haddon, R. A. (Lucite) Process for the Palladium and Phosphine Ligand Catalyzed Carbonylation of Ethylene, US 2001051745 A1, 2001.
12. Drent, E.; Jager, W. W. (Shell) Process for the carbonylation of pentenenitrile, EP 1263713 A2, 2002.
13. Drent, E.; Jager, W. W. (Shell) Process for the Carbonylation of Ethylenically Unsaturated Compounds, US 6706912 B2, 2004.
14. Eastham, G. R.; Jimenez Rodriguez, C.; Cole-Hamilton, D. J. (Lucite) Process for the Carbonylation of Ethylenically Unsaturated Compounds, US 7265240 B2, 2007.
15. Drent, E.; Ernst, R.; Jager, W. W.; Krom, C. A.; Nisbet, T. M. (Shell) Process for the Carbonylation of a Conjugated Diene to a Dicarboxylic acid, US 20080269520, 2008.
16. Jimenez Rodriguez, C.; Foster, D. F.; Eastham, G. R.; Cole-Hamilton, D. J. Chem. Commun. 2004, 1720-1721 10.1039/b404783d
17. Stempfle, F.; Quinzler, D.; Heckler, I.; Mecking, S. Macromolecules 2011, 44, 4159-4166 10.1021/ma200627e
18. Zhu, Y.; Patel, J.; Mujcinovic, S.; Jackson, W. R.; Robinson, A. J. Green Chem. 2006, 8, 746-749 10.1039/b604767j
19. Furst, M. R. L.; Seidensticker, T.; Cole-Hamilton, D. J. Green Chem. 2013, 15, 1218-1225 10.1039/c3gc37071b
20. Roesle, P.; Dürr, C. J.; Möller, H. M.; Cavallo, L.; Caporaso, L.; Mecking, S. J. Am. Chem. Soc. 2012, 134, 17696-17703 10.1021/ja307411p
21. Roesle, P.; Caporaso, L.; Schnitte, M.; Goldbach, V.; Cavallo, L.; Mecking, S. J. Am. Chem. Soc. 2014, 136, 16871-16881 10.1021/ja508447d
22. Rucklidge, A. J.; Morris, G. E.; Slawin, A. M. Z.; Cole-Hamilton, D. J. Helv. Chim. Acta 2006, 89, 1783-1800 10.1002/hlca.200690174
23. de la Fuente, V.; Waugh, M.; Eastham, G. R.; Iggo, J. A.; Castillón, S.; Claver, C. Chem.-Eur. J. 2010, 16, 6919-6932 10.1002/chem.200903158
24. Nystrom, R. F.; Brown, W. G. J. Am. Chem. Soc. 1947, 69, 1197-1199 10.1021/ja01197a060
25. Knight, J. G.; Doherty, S.; Harriman, A.; Robins, E. G.; Betham, M.; Eastham, G. R.; Tooze, R. P.; Elsegood, M. R. J.; Champkin, P.; Clegg, W. Organometallics 2000, 19, 4957-4967 10.1021/om000688o
26. Drent, E.; Ginkel, R. v.; Made, R. H. v. D. (Shell) Bidentate Ligands for the Carbonylation of Unsaturated Compounds, US 20040259724 A1, 2004.
27. McKinstry, L.; Livinghouse, T. Tetrahedron Lett. 1994, 35, 9319-9322 10.1016/S0040-4039(00)78531-5
28. Carr, N.; Dunne, B. J.; Mole, L.; Orpen, A. G.; Spencer, J. L. J. Chem. Soc., Dalton Trans. 1991, 863-871 10.1039/dt9910000863
29. Huber, J.; Mecking, S. Macromolecules 2010, 43, 8718-8723 10.1021/ma1013572
30. Knight, J. G.; Doherty, S.; Harriman, A.; Robins, E. G.; Betham, M.; Eastham, G. R.; Tooze, R. P.; Elsegood, M. R. J.; Champkin, P.; Clegg, W. Organometallics 2000, 19, 4957-4967 10.1021/om000688o
31. Neumann, H.; Sergeev, A.; Beller, M. Angew. Chem., Int. Ed. 2008, 47, 4887-4891 10.1002/anie.200800994
32. Graham, Eastham; Paul, Cameron; Robert, Tooze; Kingsley, Cavell; Peter, Edwards; Coleman, D. (Lucite) Phospha-adamantane(s) Catalytic System, US 20060106259 A1, 2006.
33. Christl, J. T.; Roesle, P.; Stempfle, F.; Muller, G.; Caporaso, L.; Cavallo, L.; Mecking, S. ChemSusChem 2014, 7, 3491-3495 10.1002/cssc.201402441
34. Doorn, J. A. V.; Snel, J. A. M.; Meijboom, N.; Wife, R. L. (Shell Oil) Polymerization Process, US 4994592, 1991.
35. Doherty, S.; Robins, E. G.; Knight, J. G.; Newman, C. R.; Rhodes, B.; Champkin, P. A.; Clegg, W. J. Organomet. Chem. 2001, 640, 182-196 10.1016/S0022-328X(01)01180-9
36. Leeuwen, P. W. N. M. v. Palladium Catalysed Carbonylation of Alkenes. In Homogeneous Catalysis: Understanding the Art; Springer: Berlin, 2004.
37. Bianchini, C.; Meli, A.; Oberhauser, W. Dalton Trans. 2003, 2627-2635 10.1039/b303502f
38. Lomas, J. S. J. Phys. Org. Chem. 2012, 25, 620-627 10.1002/poc.1953
39. Guthrie, J. P. Can. J. Chem. 1978, 56, 2342-2354 10.1139/v78-385
40. Pawelka, Z.; Haulait-Pirson, M. C. J. Phys. Chem. 1981, 85, 1052-1057 10.1021/j150608a026
41. Roesle, P.; Mecking, S. CCDC 1039378: Experimental Crystal Structure Determination, 2014; 10.5517/cc13wkbw
42. Roesle, P.; Mecking, S. CCDC 1039379: Experimental Crystal Structure Determination, 2014; 10.5517/cc13wkcx
43. Warad, I.; Azam, M.; Karama, U.; Al-Resayes, S.; Aouissi, A.; Hammouti, B. J. Mol. Struct. 2011, 1002, 107-112 10.1016/j.molstruc.2011.07.005
44. van Leeuwen, P. W. N. M. Appl. Catal., A 2001, 212, 61-81 10.1016/S0926-860X(00)00844-9
45. Tromp, M.; Sietsma, J. R. A.; van Bokhoven, J. A.; van Strijdonck, G. P. F.; van Haaren, R. J.; van der Eerden, A. M. J.; van Leeuwen, P. W. N. M.; Koningsberger, D. C. Chem. Commun. 2003, 128-129 10.1039/b206758g
46. Mulzer, J. Angew. Chem. 1987, 99, 377-378 10.1002/ange.19870990437
47. Marziano, N. C.; Sampoli, M.; Gonizzi, M. J. Phys. Chem. 1986, 90, 4347-4353 10.1021/j100409a026
48. Eastham, G. R.; Tooze, R. P.; Kilner, M.; Foster, D. F.; Cole-Hamilton, D. J. J. Chem. Soc., Dalton Trans. 2002, 1613-1617 10.1039/b201514e
49. Clegg, W.; Eastham, G. R.; Elsegood, M. R. J.; Heaton, B. T.; Iggo, J. A.; Tooze, R. P.; Whyman, R.; Zacchini, S. J. Chem. Soc., Dalton Trans. 2002, 3300-3308 10.1039/b202372p
50. 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.; Spek, A. L. J. Am. Chem. Soc. 2003, 125, 5523-5539 10.1021/ja029341y
51. Clegg, W.; Eastham, G. R.; Elsegood, M. R. J.; Heaton, B. T.; Iggo, J. A.; Tooze, R. P.; Whyman, R.; Zacchini, S. Organometallics 2002, 21, 1832-1840 10.1021/om010938g
52. Johnson, L. K.; Mecking, S.; Brookhart, M. J. Am. Chem. Soc. 1996, 118, 267-268 10.1021/ja953247i
53. Drent, E.; Kragtwijk, E. (Shell) Carbonylation of Olefins, EP 0495547 B1, 1992.
54. Holzapfel, C.; Bredenkamp, T. ChemCatChem 2015, 10.1002/cctc.201500464
55. Beckwith, A. L. J.; Bowry, V. W. J. Org. Chem. 1989, 54, 2681-2688 10.1021/jo00272a043
56. Agmon, N. Chem. Phys. Lett. 1995, 244, 456-462 10.1016/0009-2614(95)00905-J
57. Mooibroek, T. J.; Bouwman, E.; Lutz, M.; Spek, A. L.; Drent, E. Eur. J. Inorg. Chem. 2010, 2010, 298-310 10.1002/ejic.200900974
58. Marson, A.; van Oort, A. B.; Mul; Wilhelmus, P. Eur. J. Inorg. Chem. 2002, 2002, 3028-3031 10.1002/1099-0682(200211)2002:11<3028::AID-EJIC3028>3.0.CO;2-8
59. Lange, J.-P.; Price, R.; Ayoub, P. M.; Louis, J.; Petrus, L.; Clarke, L.; Gosselink, H. Angew. Chem., Int. Ed. 2010, 49, 4479-4483 10.1002/anie.201000655
60. Lange, J.-P. Green Chem. 2002, 4, 546-550 10.1039/b207546f
61. Nagai, U.; Shishido, T.; Chiba, R.; Mitsuhashi, H. Tetrahedron 1965, 21, 1701-1709 10.1016/S0040-4020(01)98640-5
62. Jones, S.; Wilson, I. Tetrahedron Lett. 2006, 47, 4377-4380 10.1016/j.tetlet.2006.04.097
63. Braga, D.; d'Agostino, S.; Grepioni, F. Organometallics 2012, 31, 1688-1695 10.1021/om200837t
64. Zacconi, F. C.; Koll, L. C.; Podestá, J. C. Tetrahedron: Asymmetry 2011, 22, 40-46 10.1016/j.tetasy.2010.12.012