Chelated bisphosphites with a calix[4]arene backbone: New ligands for rhodium-catalyzed low-pressure hydroformylation with controlled regioselectivity

Angewandte Chemie - International Edition

Volumn 38, Issue 13-14, 1999, Pages 1920-1923

  Paciello, Rocco ^a   Siggel, Lorenz ^b   Röper, Michael ^b  

^a CIH/AA T511   (Germany)

^b BASF SE   (Germany)

Author keywords

Calixarenes hydroformylations; Molecular modeling; P ligands

Indexed keywords

CALIXARENE; LIGAND; PHOSPHITE; RHODIUM;

ARTICLE; CATALYSIS; CHELATION; CHEMICAL STRUCTURE; MOLECULAR MODEL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033549542     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990712)38:13/14<1920::AID-ANIE1920>3.0.CO;2-C     Document Type: Article

References (26)

1. K. Weissermel, H.-J. Arpe. Industrielle Organische Chemie, 4th ed., VCH, Weinheim, 1994.
2. Review of technical processes: M. Beller, B. Cornils, C. D. Frohning, C. W. Kohlpaintner, J. Mol. Catal. A 1995, 104, 17-85.
3. a) T. J. Devon, G. W. Phillips, T. A. Puckette, J. L. Stavinoha, J. J. Vanderbilt (Eastman Kodak), US-A 4694109, 1987 [Chem. Abstr. 1987, 108, 7890];
4. b) 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, 5535-5543;
5. c) W. A. Herrmann, C.W. Kohlpaintner, H. Bahrmann, W. Konkol, J. Mol. Catal. 1992, 73, 191-201;
6. d) 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, 3081-3089.
7. a) E. Billig, A. G. Abatjoglou, D. R. Bryant (Union Carbide), US-A 4769498,1988[Chem. Abstr. 1989, 111, 117287];
8. b) P. Lorz, W. Bertleff, M. Röper, D. Koffer (BASF), EP-B 472071, 1992 [Chem. Abstr. 1992, 117, 34513];
9. c) G. D. Cuny, S. L. Buchwald, J. Am. Chem. Soc. 1992, 115, 2066;
10. d) A. van Rooy, P. C. J. Kamer, P. W. N. M. van Leeuwen, N. Veldman, A. L. Spek, J. Organomet. Chem. 1995, 494, C15;
11. e) 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;
12. f) A. van Rooy, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. Organomet. Chem. 1997, 535, 201.
13. For the synthesis and application of calixarenes, see "Calixarenes": C. D. Gutsche in Monographs in Supramolecular Chemistry, Vol. 1 (Ed.: J. F. Stoddart), The Royal Society of Chemistry, Cambridge, 1989.
14. Review: C. Wieser, C. Dieleman, D. Mat, Coord. Chem. Rev. 1997, 165, 93. These OH groups are capable, possibly after derivatization, of complexing metal ions in a host-guest reaction.
15. Phosphorus-containing ligands based on calix[4]arenes: a) D. Jacoby, C. Floriani, A. Chiesi-Villa, C. Rizzoli, J. Chem. Soc. Dalton Trans. 1993, 813;
16. b) C. Loeber, D. Matt (École Européenne des Hautes Études des Industries Chimiques de Strasbourg), FR-B 2717480, 1995 [Chem. Abstr. 1996, 124, 133985];
17. c) C. Loeber, D. Matt, A. De Cian, J. Fischer, J. Organomet. Chem. 1994, 475, 297-305;
18. d) C. Loeber, C. Wieser, D. Matt, A. De Cian, J. Fischer, L. Toupet, Bull. Soc. Chim. Fr. 1995, 132, 166.
19. C. Wieser-Jeunesse, D. Matt, A. De Cian, Angew. Chem. 1998, 110, 3027; Angew. Chem. Int. Ed. 1998, 37, 2861.
20. C. Wieser-Jeunesse, D. Matt, A. De Cian, Angew. Chem. 1998, 110, 3027; Angew. Chem. Int. Ed. 1998, 37, 2861.
21. R. Paciello, M. Röper, H.-J. Kneuper, E. Langguth (BASF), DE-B 4321194, 1995 [Chem. Abstr. 1995, 122, 160937].
22. Regioselectivity [%] = [yield(1-nonanal)/total yield(nonanals)] × 100.
23. The molecular modeling method is described in: R. Paciello, L. Siggel, N. Walker, M. Röper, J. Mol. Catal. A 1999, 143, 85.
24. 3; cf.: K. Sasse, Methoden Org. Chem. (Houben-Weyl), 4th ed. 1952-, 1964, Vol. XII/2, p. 12.
25. In the meantime it has been shown that ligands 1-4 are also suitable for the nickel-catalyzed hydrocyanation: T. Foo, J. M. Garner, R. Shapiro, W. Tam, WO-A 9622968 (Du Pont), 1996 [Chem. Abstr. 1996, 125, 195996].
26. Methods such as the determination of the "natural bite angle" implicitly address the problem of electronic properties by searching for ligands that stabilize special structures such as trigonal-bipyramidal rhodium complexes; see also references [3b, 3d, 4f].