Multicomponent Porphyrin Assemblies as Functional Bidentate Phosphite Ligands for Regioselective Rhodium-Catalyzed Hydroformylation

Angewandte Chemie - International Edition

Volumn 42, Issue 45, 2003, Pages 5619-5623

  Slagt, Vincent F ^a   Van Leeuwen, Piet W N M ^a   Reek, Joost N H ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

Homogenous catalysis; Hydroformylation; Porphyrinoids; Self assembly; Supramolecular chemistry

Indexed keywords

ALDEHYDES; CATALYST SELECTIVITY; PORPHYRINS; RHODIUM; STRUCTURE (COMPOSITION);

HYDROFORMYLATION;

SUPRAMOLECULAR CHEMISTRY;

PHOSPHITE; PORPHYRIN; RHODIUM; ZINC DERIVATIVE;

ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; HYDROGEN BOND; MOLECULAR INTERACTION; MOLECULAR MECHANICS; MOLECULAR SIZE; NANOPARTICLE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUPRAMOLECULAR CHEMISTRY;

EID: 0345530069     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352525     Document Type: Article

References (74)

1. L. J. Prins, D. N. Reinhoudt, P. Timmerman, Angew. Chem. 2001, 113, 2446; Angew. Chem. Int. Ed. 2001, 40, 2382.
2. L. J. Prins, D. N. Reinhoudt, P. Timmerman, Angew. Chem. 2001, 113, 2446; Angew. Chem. Int. Ed. 2001, 40, 2382.
3. a) B. Olenyuk, J. A. Whiteford, A. Fechtenkötter, P. J. Stang, Nature 1999, 398, 796;
4. b) M. Fujita, N. Fujita, K. Ogura, K. Yamaguchi, Nature 1999, 400, 52;
5. c) L. J. Prins, J. Huskens, F. de Jong, P. Timmerman, D. N. Reinhoudt, Nature 1999, 398, 498;
6. d) N. Takeda, K. Umemoto, K. Yamaguchi, M. Fujita, Nature 1999, 398, 794;
7. e) K. A. Jolliffe, P. Timmerman, D. N. Reinhoudt, Angew. Chem. 1999, 111, 983; Angew. Chem. Int. Ed. 1999, 38, 933;
8. e) K. A. Jolliffe, P. Timmerman, D. N. Reinhoudt, Angew. Chem. 1999, 111, 983; Angew. Chem. Int. Ed. 1999, 38, 933;
9. f) L. R. MacGillivray, J. L. Atwood, Nature 1997, 389, 469;
10. g) L. J. Prins, F. de Jong, P. Timmerman, D. N. Reinhoudt, Nature 2000, 408, 181.
11. a) J.-M. Lehn in Supramolecular Chemistry: Concepts and Perspectives, VCH, Weinheim, 1995;
12. b) M. Ortega Lorenzo, C. J. Baddeley, C. Muryn, R. Raval, Nature 2000, 404, 376;
13. c) J. L. Atwood, L. J. Barbour, M. J. Hardie, C. L. Raston, Coord. Chem. Rev. 2001, 222, 3;
14. d) G. F. Swiegers, T. J. Malefetse, Chem. Rev. 2000, 100, 3483;
15. e) M. Albrecht, Chem. Rev. 2001, 101, 3457;
16. f) S. Leininger, B. Olenyuk, P. J. Stang, Chem. Rev. 2000, 100, 853;
17. g) B. J. Holliday, C. A. Mirkin, Angew. Chem. 2001, 113, 2076; Angew. Chem. Int. Ed. 2001, 40, 2022.
18. g) B. J. Holliday, C. A. Mirkin, Angew. Chem. 2001, 113, 2076; Angew. Chem. Int. Ed. 2001, 40, 2022.
19. a) D. N. Reinhoudt, M. Crego-Calama, Science, 2002, 295, 2403;
20. b) O. Ikkala, G. ten Brinke, Science, 2002, 295, 2407;
21. c) G. R. Desiraju, Nature, 2001, 412, 397;
22. c) R. F. Service, Science 2001 293, 782.
23. For reviews see: a) J. K. M. Sanders, Chem. Eur. J. 1998, 4, 1378;
24. b) P. D. Beer, P. A. Gale, Angew. Chem. 2001, 113, 502; Angew. Chem. Int. Ed. 2001, 40, 486;
25. b) P. D. Beer, P. A. Gale, Angew. Chem. 2001, 113, 502; Angew. Chem. Int. Ed. 2001, 40, 486;
26. c) M. C. Feiters, in Compr. Supramol. Chem., Vol. 10, Elsevier, Oxford 1996, 267;
27. d) R. Breslow, S. D. Dong, Chem. Rev. 1998, 98, 1997;
28. e) K. Takahashi, Chem. Rev. 1998, 98, 2013;
29. f) W. B. Motherwell, M. J. Bingham, Y. Six, Tetrahedron, 2001, 57, 4663;
30. g) M. T. Reetz, Top Catal. 1997, 4, 187;
31. h) Y. Murakami, J.-I Kikuchi, Y. Hisaeda, O. Hayashida, Chem. Rev. 1996, 96, 721.
32. a) R. Wyler, J. de Mendoza, J. Rebek Jr., Angew. Chem. 1993, 105, 1820; Angew. Chem. Int. Ed. Engl. 1993, 32, 1699;
33. a) R. Wyler, J. de Mendoza, J. Rebek Jr., Angew. Chem. 1993, 105, 1820; Angew. Chem. Int. Ed. Engl. 1993, 32, 1699;
34. b) M. Morgan, J. RebekJr., Chem. Rev. 1997, 97, 1647-1668;
35. c) J. Rebek Jr., Chem. Soc. Rev. 1996, 25, 255-264;
36. d) J. Rebek Jr., Chem. Commun. 2000, 637-643;
37. e) F. Hof, S.L. Craig, C. Nuckolls, J. Rebek Jr., Angew. Chem. 2002, 114, 1556; Angew. Chem. Int. Ed. 2002, 41, 1488;
38. e) F. Hof, S.L. Craig, C. Nuckolls, J. Rebek Jr., Angew. Chem. 2002, 114, 1556; Angew. Chem. Int. Ed. 2002, 41, 1488;
39. f) A. Jasat, J. C. Sherman, Chem. Rev. 1999, 99, 931;
40. g) L. R. MacGillivray, J. L. Atwood, Angew. Chem. 1999, 111, 1080; Angew. Chem. Int. Ed. 1999, 38, 1018;
41. g) L. R. MacGillivray, J. L. Atwood, Angew. Chem. 1999, 111, 1080; Angew. Chem. Int. Ed. 1999, 38, 1018;
42. h) C. J. Jones, Chem. Soc. Rev. 1998, 27, 289.
43. a) J. Kang, J. Rebek Jr., Nature, 1997, 385, 50;
44. b) J. Kang, G. Hilmersson, J. Santamaria, J. Rebek Jr., J. Am. Chem. Soc. 1998, 120, 3650;
45. c) J. Kang, J. Santamaria, G. Hilmersson, J. Rebek Jr., J. Am. Chem. Soc. 1998, 120, 7389;
46. d) M. Yoshizawa, T. Kusukawa, M. Fujita, S. Sakamoto, K. Yamaguchi, J. Am. Chem. Soc. 2001, 123, 10454;
47. e) M. Yoshizawa, Y. Takeyama, T. Okano, M. Fujita, J. Am. Chem. Soc. 2003, 125, 3243;
48. f) M. Yoshizawa, Y. Takeyama, T. Kusukawa, M. Fujita, Angew. Chem. 2002, 114, 1403; Angew. Chem. Int. Ed., 2002, 41, 1347;
49. f) M. Yoshizawa, Y. Takeyama, T. Kusukawa, M. Fujita, Angew. Chem. 2002, 114, 1403; Angew. Chem. Int. Ed., 2002, 41, 1347;
50. g) R. Warmuth, J. L. Kerdelhue, S. S. Carrera, K. J. Langenwalter, N. Brown, Angew. Chem. 2002, 114, 102; Angew. Chem. Int. Ed., 2002, 41, 96.
51. g) R. Warmuth, J. L. Kerdelhue, S. S. Carrera, K. J. Langenwalter, N. Brown, Angew. Chem. 2002, 114, 102; Angew. Chem. Int. Ed., 2002, 41, 96.
52. a) V. F. Slagt, J. N. H. Reek, P. C. J. Kamer, P. W. N. M. van Leeuwen, Angew. Chem. 2001, 113, 4401; Angew. Chem. Int. Ed. 2001, 40, 4271;
53. a) V. F. Slagt, J. N. H. Reek, P. C. J. Kamer, P. W. N. M. van Leeuwen, Angew. Chem. 2001, 113, 4401; Angew. Chem. Int. Ed. 2001, 40, 4271;
54. b) G. A. Morris, S. T. Nguyen, J. T. Hupp, J. Mol. Catal. A: Chem. 2001, 174, 15;
55. c) M. L. Merlau, M. Del. Pilar Meija, S. T. Nguyen, J. T. Hupp, Angew. Chem. 2001, 113, 4369; Angew. Chem. Int. Ed. 2001, 40, 4239.
56. c) M. L. Merlau, M. Del. Pilar Meija, S. T. Nguyen, J. T. Hupp, Angew. Chem. 2001, 113, 4369; Angew. Chem. Int. Ed. 2001, 40, 4239.
57. a) N. Bampos, V. Marvaud, J. K. M. Sanders, Chem. Eur. J. 1998, 4, 335;
58. b) C. C. Mak, N. Bampos, J. K. M. Sanders, Angew. Chem. 1998, 110, 3169; Angew. Chem. Int. Ed. 1998, 37, 3020;
59. b) C. C. Mak, N. Bampos, J. K. M. Sanders, Angew. Chem. 1998, 110, 3169; Angew. Chem. Int. Ed. 1998, 37, 3020;
60. c) C. C. Mak, N. Bampos, S. L. Darling, M. Montalti, L. Prodi, J. K. M. Sanders, J. Org. Chem. 2001, 66, 4476;
61. d) C. A. Hunter, M. N. Meah, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5773;
62. e) C. A. Hunter, M. N. Meah, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5780.
63. At these concentrations the formation of larger assemblies is unlikely, and indeed the spectroscopic data did not indicate formation of such species.
64. We have analyzed the titration curves with a fitting program developed by Hunter et al.: A. P. Bisson, C. A. Hunter, J. Carlos, K. Young, Chem. Eur. J. 1998, 4, 845.
65. 2] with (zinc(1I) porphyrin)phosphite 1 in a 1:2 ratio.
66. These signals are similar to those found for other phosphite rhodium complexes: a) G. J. H. Buisman, E. Vos, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. Chem. Soc. Dalton Trans. 1995, 409;
67. b) A. van Rooy, P. C. J. Kamer, P. W. N. M. van Leeuwen, Organometallics 1996, 15, 835.
68. P. W. N. M. van Leeuwen, C. Claver, in Rhodium-catalyzed Hydroformylation, Kluwer, Dordrecht, 2000.
69. A. van Rooy, P. C. J. Kamer, P. W. N. M. van Leeuwen, Organometallics 1996, 15, 835.
70. During the preparation of this manuscript a chelating bisphosphane based on hydrogen bonds yielding highly selective hydroformylation catalysts was reported: B. Breit, W. Seiche, J. Am. Chem. Soc. 2003, 125, 6608.
71. Usually the l/b ratio decreases at lower temperatures: a) R. Lazzaroni, R. Settambolo, G. Uccello-Barretta, A. Caiazzo, Organometallics 1996, 15, 4657;
72. b) C. Botteghi, L. Cazzolato, M. Marchetti, S. Paganelli, J. Org. Chem. 1995, 60, 6612.
73. G. Szintay, A. Horvath, Inorg. Chim. Acta 2000, 310, 175.
74. S. C. van der Slot, J. Duran, J. Luten, P. C. J. Kamer, P. W. N. M. van Leeuwen, Organometallics 2002, 21, 3873.