Synthesis, complexation behavior and application of a new diphosphite ligand in rhodium-catalyzed hydroformylation

Journal of Organometallic Chemistry

Volumn 696, Issue 19, 2011, Pages 3050-3057

  Mikhel, Igor S ^a   Dubrovina, Natalia V ^a   Shuklov, Ivan A ^a   Baumann, Wolfgang ^a   Selent, Detlef ^a   Jiao, Haijun ^a   Christiansen, Andrea ^b   Franke, Robert ^b   Börner, Armin ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b Evonik Oxeno GmbH   (Germany)

Author keywords

Diphosphite; Homogeneous catalysis; Hydroformylation; Palladium; Platinum; Rhodium

Indexed keywords

AS-LIGANDS; BINAPHTHOL; DIPHOSPHITE; DIPHOSPHITE LIGANDS; HOMOGENEOUS CATALYSIS; MASS SPECTROMETRY DATA; METHYL ESTERS; OXIDATIVE COUPLINGS; PROPIONIC ACIDS; RHODIUM CATALYSTS; RHODIUM-CATALYZED HYDROFORMYLATION;

CATALYSIS; CATALYST SELECTIVITY; CHELATION; COMPLEXATION; FATTY ACIDS; HYDROFORMYLATION; HYDROXYLATION; LIGANDS; MASS SPECTROMETRY; METAL COMPLEXES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM; PLATINUM; REACTION KINETICS; RHODIUM; STYRENE;

RHODIUM COMPOUNDS;

EID: 79960910006     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2011.05.004     Document Type: Article

References (73)

1. P.W.N.M. van Leeuwen, and G. van Koten J.A. Moulijn, P.W.N.M. van Leeuwen, R.A. van Santen, Catalysis: An Integrated Approach to Homogeneous, Heterogeneous and Industrial Catalysis 1993 Elsevier Amsterdam 201 222
2. M. Beller, B. Cornils, C.D. Frohning, and C.W. Kohlpaintner J. Mol. Cat. A Chem. 104 1995 17 85
3. C.D. Frohning, and C.W. Kohlpaintner B. Cornils, W.A. Herrmann, Applied Homogeneous Catalysis with Organometallic Compounds: A Comprehensive Handbook in Two Volumes vol. 1 1996 VCH Verlagsgesellschaft Weinheim 27 104
4. P.W.N.M. van Leeuwen, and C. Claver Rhodium Catalyzed Hydroformylation 2000 Kluwer Dordrecht
5. G. Protzmann, and K.-D. Wiese Erdöl, Erdgas, Kohle 117 2001 235 240
6. K.-D. Wiese, and D. Obst Top. Organomet. Chem. 18 2006 1 33
7. E. Billig, A.G. Abatjoglou, D.R. Bryant, (UCC), EP 213639 (1987), EP 214622(1987), US 4769498 (1988).
8. S. Keiichi, Y. Kawaragi, M. Takai, T. Ookoshi (Mitsubishi Kasei), EP 518241 (1992).
9. G.D. Cuny, and S.L. Buchwald J. Am. Chem. Soc. 115 1993 2066 2068
10. B. Moasser, W.L. Gladfelter, and D.C. Roe Organometallics 14 1995 3832 3838
11. A. van Rooy, P.C.J. Kamer, and P.W.N.M. van Leeuwen J. Organomet. Chem. 535 1997 201 207
12. D. Röttger, A. Börner, D. Selent, D. Hess (Oxeno), DE 10031493 (2002).
13. M.A. Brammer, W.-J. Peng, J.M. Maher (Dow Chemica), WO 2008124468 (2008).
14. T.C. Eisenschmid, R.R. Peterson, G.A. Miller, A. G. Abatjoglou (UCC), WO 2008115740 (2008).
15. Selent, A. Börner, B. Kreidler, D. Hess, K.-D. Wiese (Oxeno), WO 2008071508 (2008).
16. W.-J. Peng, C.L. Rand (Dow Chemical), WO 2008134326 (2008).
17. For related ligands, which have been used widely in asymmetric hydroformylation, see the following review A. Gual, C. Godard, S. Castillon, and C. Claver Tetrahedron: Asymmetry 21 2010 1135 1146 and ref. cited therein
18. K.H. Pawlowski, and B. Schartel Polym. Int. 56 2007 1404 1414
19. For some typical results, see
20. D. Selent, D. Röttger, K.-D. Wiese, and A. Börner Angew. Chem. Int. Ed. 39 2000 1639 1641
21. D. Selent, D. Hess, K.-D. Wiese, D. Röttger, C. Kunze, and A. Börner Angew. Chem. Int. Ed. 40 2001 1696 1698
22. C. Kunze, D. Selent, R. Schmutzler, I. Neda, A. Spannenberg, and A. Börner Heteroatom Chem. 12 2001 577 585
23. C. Kunze, D. Selent, I. Neda, R. Schmutzler, W. Baumann, and A. Börner Z. Allgem. Anorg. Chem. 628 2002 779 787
24. D. Selent, W. Baumann, R. Kempe, A. Spannenberg, D. Röttger, K.D. Wiese, and A. Börner Organometallics 22 2003 4265 4271
25. D. Selent, K.D. Wiese, and A. Börner O-Acylphosphites: new and promising ligands for isomerising hydroformylation J.R. SowaJr, Cat. Org. React. 2005 Taylor & Francis Boca Raton 459 469
26. D. Selent, W. Baumann, K.-D. Wiese, and A. Börner Chem. Commun. 2008 6203 6205
27. I.A. Shuklov, N.V. Dubrovina, H. Jiao, A. Spannenberg, and A. Börner Eur. J. Org. Chem. 2010 1669 1680
28. Delivered by UFC Corporation, Taiwan.
29. I.M. Malkowsky, C.E. Rommel, K. Wedeking, R. Fröhlich, K. Bergander, M. Nieger, C. Quaiser, U. Griesbach, H. Pütter, and S.R. Waldvogel Eur. J. Org. Chem. 2006 241 245
30. A. Kirste, M. Nieger, I.M. Malkowsky, F. Stecker, A. Fischer, and S.R. Waldvogel Chem. Eur. J. 15 2009 2273 2277
31. For a review, compare I.A. Shuklov, N.V. Dubrovina, and A. Börner Synthesis 2007 2925 2943
32. I. Malnar, and C.J. Sih Tetrahedron Lett. 41 2000 1907 1911
33. S. Ciecholewski, E. Hammer, K. Manda, G. Bose, V.T.H. Nguyen, P. Langer, and F. Schauer Tetrahedron 61 2005 4615 4619
34. A. Gesell, M. Rolf, J. Ziegler, M.L. Díaz Chávez, F.-C. Huang, and T.M. Kutchan J. Biol. Chem. 284 2009 24432 24442
35. M.F. Semmelhack, P.M. Helquist, and L.D. Jones J. Am. Chem. Soc. 93 1971 5908 5910
36. M.F. Semmelhack, P. Helquist, L.D. Jones, L. Keller, L. Mendelson, L. Speltz Ryono, J. Gorzynski Smith, and R.D. Stauffer J. Am. Chem. Soc. 103 1981 6460 6471
37. M. Lourak, R. Vanderesse, Y. Fort, and P. Caubére J. Organomet. Chem. 54 1989 4840 4844
38. J. Ishida, M. Kozuka, H. Tokuda, H. Nishino, S. Nagumo, K.-H. Lee, and M. Nagai Bioorg. Med. Chem. 10 2002 3361 3365
39. D.R. Armstrong, C. Cameron, D.C. Nonhebel, and P.G. Perkins J. Chem. Soc. Perkin Trans. 2 1983 563 568
40. K. Ding, Y. Wang, L. Zhang, and Y. Wu Tetrahedron 52 1996 1005 1010
41. P.J. Wallis, K.J. Booth, A.F. Patti, and J.L. Scott Green Chem. 8 2006 333 337
42. A.M. Guidote, K.-I. Ando, K. Terada, Y. Kurusu, H. Nagao, and Y. Masuyama Inorg. Chim. Acta 324 2001 203 211
43. M. Ogata, K. Shin-Ya, S. Urano, and T. Endo Chem. Pharm. Bull. 53 2005 344 346
44. A. Alexakis, D. Polet, S. Rosset, and S. March J. Org. Chem. 69 2004 5660 5667
45. G. Delogu, M.A. Dettori, A. Patti, S. Pedotti, A. Forni, and G. Casalone Tetrahedron: Asymmetry 14 2003 2467 2474
46. K. Wang, M. Lü, A. Yu, X. Zhu, and Q. Wang J. Org. Chem. 74 2009 935 938
47. J.I. van der Vlugt, A.C. Hewat, S. Neto, R. Sablong, A.M. Mills, M. Lutz, A.L. Spek, C. Müller, and D. Vogt Adv. Synth. Catal. 346 2004 993 1003
48. L. Panella, J. Bross, J. Jin, M.W. Fraaije, D.B. Janssen, M. Jeronimus-Stratingh, B.L. Feringa, A.J. Minnaard, and J.G. De Vries Chem. Commun. 2005 5656 5658
49. R. Jana, and J.A. Tunge Org. Lett. 11 2009 971 974
50. H.A. Albert J. Am. Chem. Soc. 76 1954 4983 4985
51. S.D. Pastor, S.P. Shum, A.D. DeBellis, L.P. Burke, R.K. Rodebaugh, F.H. Clarke, and G. Riehs Inorg. Chem. 35 1996 949 958
52. G.J.H. Buisman, L.A. van der Veen, A. Klootwihk, W.G.J. de Lange, P.C.J. Kamer, P.W.N.M. van Leeuwen, and D. Vogt Organometallics 16 1997 2929 2939
53. J.-C. Hierso, A. Fihri, V.V. Ivanov, B. Hanquet, N. Pirio, B. Donnadieu, B. Rebire, R. Amardeil, and P. Meunier J. Am. Chem. Soc. 126 2004 11077 11087
54. J.-C. Hierso, D. Armspach, and D. Matt Compt. Rendus Chimie 12 2009 1002 1013
55. I. Piras, R. Jennerjahn, R. Jackstell, W. Baumann, A. Spannenberg, R. Franke, K.-D. Wiese, and M. Beller J. Organomet. Chem. 695 2010 479 486
56. A. van Rooy, P.C.J. Kamer, P.W.N.M. van Leeuwen, K. Goubitz, J. Fraanje, N. Veldman, and A.L. Spek Organometallics 15 1996 835 847
57. E.K. van den Beuken, W.G.J. de Lange, P.W.N.M. van Leeuwen, N. Veldman, A.L. Spek, and B.L. Feringa J. Chem. Soc. Dalton Trans. 1996 3561 3569
58. C.J. Cobley, R.D.J. Froese, J. Klosin, C. Qin, and G.T. Whiteker Organometallics 26 2007 2986 2999
59. L. Pignataro, B. Lynikaite, R. Colombo, S. Carboni, M. Krupicka, U. Piarulli, and C. Gennari Chem. Commun. 2009 3539 3541
60. N. Ahmad, E.W. Ainscough, T.A. James, and S.D. Robinson J. Chem. Soc. Dalton Trans. 1973 1148
61. C.J. Cobley, and P.G. Pringle Inorg. Chim. Acta 265 1997 107 115
62. R. Kadyrov, D. Heller, and R. Selke Tetrahedron: Asymmetry 9 1998 329 340
63. S. Cserepi-Szucs, G. Huttner, L. Zsolnai, and J. Bakos J. Organomet. Chem 586 1999 70 78
64. P. Maji, S.S. Krishnamurthy, and M. Nethaji Polyhedron 27 2008 3519 3527
65. A. Albinati, F. Lianza, H. Berger, P.S. Pregosin, H. Rüegger, and R.W. Kunz Inorg. Chem. 32 1993 478 486
66. I.S. Mikhel, K.N. Gavrilov, A.I. Polosukhin, and A.I. Rebrov Russ. Chem. Bull. (Engl. Transl.) 47 1998 1585
67. I.S. Mikhel, K.N. Gavrilov, and A.I. Rebrov Russ. J. Inorg. Chem. (Engl. Transl.) 44 1999 1551
68. I.S. Mikhel, O.G. Bondarev, V.N. Tsarev, G.V. Grinselev-Knyazev, K.A. Lyssenko, V.A. Davankov, and K.N. Gavrilov Organometallics 22 2003 925 930
69. For some recent results, compare
70. B. El Ali, J. Tijani, M. Fettouhi, A. Al-Arfaj, and M. El-Faer Appl. Organomet. Chem. 19 2005 329 338
71. S. Yu, Y. Chie, Z. Guan, Y. Zou, W. Li, and X. Zhang Org. Lett. 11 2009 241 244
72. A.G. Panda, M.D. Bhor, S.S. Ekbote, and B.M. Bhanage Cat. Lett. 131 2009 649 655
73. S. Akai, T. Ikawa, S. Takayanagi, Y. Morikawa, S. Mohri, M. Tsubakiyama, M. Egi, Y. Wada, and Y. Kita Angew. Chem. Int. Ed. 47 2008 7673 7676