Sterically demanding diphosphonite ligands - Synthesis and application in nickel-catalyzed isomerization of 2-methyl-3-butenenitrile

Advanced Synthesis and Catalysis

Volumn 346, Issue 8, 2004, Pages 993-1003

  Van Der Vlugt, Jarl Ivar ^a   Hewat, Alison C ^a   Neto, Samuel ^a   Sablong, Rafael ^a   Mills, Allison M ^b   Lutz, Martin ^b   Spek, Anthony L ^b   Müller, Christian ^a   Vogt, Dieter ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

2 methyl 3 butenenitrile; Hydrocyanation; Isomerization; Nickel; P ligands

Indexed keywords

1,3 BUTADIENE; NICKEL; NITRILE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CRYSTAL STRUCTURE; CYANATION; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 4344709593     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303240     Document Type: Article

References (54)

1. a) S. Krill, in: Applied Homogeneous Catalysis with Organometallic Compounds; (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 2002, 468;
2. b) A. L. Casalnuovo, T. V. RajanBabu, Transition Metals for Organic Synthesis 1998, 1, 91;
3. c) T. V. RajanBabu, A. L. Casalnuovo, in: Comprehensive Asymmetric Catalysis, Vol. 1, Springer, Heidelberg, Berlin, 1999, 367;
4. d) H. E. Bryndza, J. A. Harrelson Jr., in: Aqueous-Phase Organometallic Catalysis, (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 1998, 393;
5. e) C. A. Tolman, R. J. McKinney, W. C. Seidel, J. D. Druliner, W. R. Stevens, Adv. Catal. 1985, 33, 1.
6. W. Goertz, P. C. J. Kamer, P. W. N. M. van Leeuwen, D. Vogt, Chem. Commun. 1997, 1521.
7. W. Goertz, W. Keim, D. Vogt, U. Englert, M. D. K. Boele, L. A. van der Veen, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. Chem. Soc. Dalton Trans. 1998, 2981.
8. C. A. Tolman and J. W. Faller, in: Homogeneous Catalysis with Metal Phosphine Complexes; (Ed.: L. H. Pignolet), Plenum, New York, 1983, 81.
9. M. Beller, B. Cornils, C. D. Frohning, C. W. Kohlpainter, J. Mol. Cat. A: Chem. 1995, 104, 17.
10. For recent reviews, see: F. Ungvary, Coord. Chem. Rev. 2002, 218, 1; P. W. N. M. van Leeuwen, C. P. Casey, G. T. Whiteker, in: Rhodium catalyzed hydroformylation, (Eds.: P. W. N. M. van Leeuwen, C. Claver), Kluwer, Amsterdam, 2001, 63.
11. For recent reviews, see: F. Ungvary, Coord. Chem. Rev. 2002, 218, 1; P. W. N. M. van Leeuwen, C. P. Casey, G. T. Whiteker, in: Rhodium catalyzed hydroformylation, (Eds.: P. W. N. M. van Leeuwen, C. Claver), Kluwer, Amsterdam, 2001, 63.
12. a) T. J. Devon, G. W. Phillips, T. A. Puckette, J. L. Stavinoha, J. J. Vanderbilt, (to Eastman Kodak), U. S. Patent 4,694,109, 1987; Chem. Abstr. 1988, 108, 7890;
13. b) T. J. Devon, G. W. Phillips, T. A. Puckette, J. L. Stavinoha, J. J. Vanderbilt, (to Eastman Kodak), U. S. Patent 5,332,846, 1994; Chem. Abstr. 1994, 121, 280879.
14. H. Bahrmann, P. Lappe, W. A. Herrmann, G. P. Albanese, R. B. Manetsberger, (to Hoechst AG), Eur. Patent 646,588, 1994; Chem. Abstr. 1995, 123, 112408.
15. P. W. N. M. van Leeuwen, P. A. M. Grotenhuis, B. L. Goodall, (to Shell), Eur. Patent 309,056, 1989; Chem. Abstr. 1989, 111, 232086.
16. C. P. Casey, G. T. Whiteker, M. G. Melville, L. M. Petrovich, J. A. Gavney Jr., D. R. Powell, J. Am. Chem. Soc. 1992, 114, 5535.
17. E. Billig, A. G. Abatjoglou, D. R. Bryant, (to Union Carbide), U. S. Patents 4,769,498, 4,668,651, and 4,748,261, 1987; Chem. Abstr. 1987, 14, 3081.
18. K. Sato, Y. Karawagi, M. Takai, T. Ookoshi, (to Mitsubishi), U. S. Patent 5,235,113, 1993; Chem. Abstr. 1993, 118, 191183.
19. A. van Rooy, P. C. J. Kamer, P. W. N. M. van Leeuwen, K. Goubitz, J. Fraanje, N. Veldman, A. L. Spek, Organometallics 1996, 15, 835.
20. a) M. T. Reetz, A. Gosberg, R. Goddard, S. H. Kyung, Chem. Commun. 1998, 2077;
21. b) M. T. Reetz, D. Moulin, A. Gosberg, Org. Lett. 2001, 3, 4083;
22. c) A. Zanotti-Gerosa, C. Malan, D. Herzberg, Org. Lett. 2001, 3, 3687.
23. S. Hillebrand, J. Bruckmann, C Krüger, M. W. Haenel, Tetrahedron Lett. 1995, 36, 75.
24. M. Kranenburg, Y. E. M. van der Burgt, P. C. J. Kamer, P. W. N. M. van Leeuwen, K. Goubitz, J. Fraanje, Organometallics 1995, 14, 3081.
25. a) A. C. Hewat, PhD thesis, 2000, RWTH Aachen, Germany;
26. b) W. Ahlers, D. Wiebelhaus, R. Paciello, M. Bartsch, R. Baumann, D. Vogt, A. C. Hewat, (to BASF AG) WO 222,261, 2002; Chem. Abstr. 2002, 136, 249380.
27. W. Goertz, P. C. J. Kamer, P. W. N. M. van Leeuwen, D. Vogt, Chem. Eur. J. 2001, 1614.
28. A. Buhling, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. W. Elgersma, K. Goubitz, J. Fraanje, Organometallics 1997, 16, 3027.
29. A. L. Casalnuovo, T. V. RajanBabu, T. A. Ayers, T. H. Warren, J. Am. Chem. Soc. 1984, 106, 9869.
30. J. I. van der Vlugt, R. Sablong, A. M. Mills, H. Kooijman, A. L. Spek, A. Meetsma, D. Vogt, J. Chem. Soc. Dalton Trans. 2003, 4690.
31. J. A. J. Jarvis, R. H. B Mais, P. G. Owston, J. Chem. Soc. A. 1968, 1473.
32. L. J. Guggenberger, Inorg. Chem. 1973, 12, 499.
33. I. M. Angulo, E. Bouwman, M. Lutz, W. P. Mul, A. L. Spek, Inorg. Chem. 2001, 40, 2073.
34. D. J. Spielvogel, W. M. Davis, S. L. Buchwald, Organometallics 2002, 21, 3833.
35. F. H. Allen, O. Kennard, Chem. Des. Autom. News 1993, 8, 31.
36. a) C. A. Tolman, W. C. Seidel, D. H. Gerlach, J. Am. Chem. Soc. 1972, 94, 2669;
37. b) D. G. Dick, D. W. Stephan, C. F. Campana, Can. J. Chem. 1990, 68, 628.
38. a) P. C. J. Kamer, J. N. H. Reek, P. W. N. M. van Leeuwen, Acc. Chem. Res. 2001, 34, 895;
39. b) P. W. N. M. van-Leeuwen, P. C. J. Kamer, J. N. H. Reek, P. Dierkes, Chem. Rev. 2000, 100, 2741.
40. a) L. A. van der Veen, P. K. Keeven, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. Chem. Soc. Dalton Trans. 2000, 2105;
41. b) L. A. van der Veen, P. C. J. Kamer, P. W. N. M. van Leeuwen, Angew. Chem. Int. Ed. 1999, 38, 336.
42. W. Goertz, PhD. Thesis 1998, RWTH Aachen, Germany.
43. a) R. J. McKinney, W. A. Nugent, Organometallics 1989, 8, 2871;
44. b) R. J. McKinney, R. B. Osborne, (to DuPont de Nemours), U. S. Patent 4,874,884, 1989; Chem. Abstr. 1990, 112, 18038.
45. Y. T. Chia, W. C. Drinkard, E. N. Squire, (to DuPont de Nemours), U. S. Patent 3,766,237, 1973; Chem. Abstr. 1974, 80, 70373.
46. N. M. Brunkan, W. D. Jones, J. Organomet. Chem. 2003, 683, 77.
47. J. Wilting, A. C. Hewat, C. Müller, J. I. van der Vlugt, D. M. Tooke, D. D. Ellis, A. L. Spek, D. Vogt, manuscript in preparation.
48. C. A. Tolman, J. Chem. Edu. 1986, 3, 199.
49. J. I. van der Vlugt, R. Sablong, P. C. M. M. Magusin, A. M. Mills, A. L. Spek, D. Vogt, Chem. Eur. J. submitted for publication.
50. B. Bogdanovic, M. Kröner, G. Wilke, Liebigs Ann. Chem. 1966, 699, 1.
51. G. M. Sheldrick, SHELXS97, University of Göttingen, Germany, 1997.
52. P. T. Beurskens, G. Admiraal, G Beurskens, W. P. Bosman, S. García-Granda, R. O. Gould, J. M. M. Smits, C. Smykalla, The DIRDIF99 program system, University of Nijmegen, The Netherlands, 1999.
53. G. M. Sheldrick, SHELXL97, University of Göttingen, Germany, 1997.
54. A. L. Spek, J. Appl. Cryst. 2003, 36, 7.