Re-based heterogeneous catalysts for olefin metathesis prepared by surface organometallic chemistry: Reactivity and selectivity

Chemistry - A European Journal

Volumn 9, Issue 4, 2003, Pages 971-975

  Chabanas, Mathieu ^a   Copéret, Christophe ^a   Basset, Jean Marie ^a  

^a UMR 5265   (France)

Author keywords

Functionalized olefins; Heterogeneous catalysis; Metathesis; Rhenium; Silica

Indexed keywords

ALUMINA; CATALYSIS; OLEFINS; RHENIUM COMPOUNDS; SILICA;

OLEFIN METATHESIS;

CATALYST ACTIVITY;

3,3 DIMETHYLBUTENE; 4,4 DIMETHYLPENT 2 ENE; ALKENE; ALUMINUM OXIDE; ISOBUTYLENE; PROPYLENE; RHENIUM; SILICON DIOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; METAL BINDING; ORGANIC CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0037450125     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200390119     Document Type: Article

References (50)

1. a) H. S. Euleterio, US Patent, 3074918, 1963;
2. b) R. L. Banks, G. C. Bailey, Ind. Eng. Chem. Prod. Res. Dev. 1964, 3, 170;
3. In fact there is earlier evidence for that the discovery of that reaction in polymer chemistry (ROMP): A. W. Anderson, N. G. Merckling, US Patent 2721189, 1955; I. M. Robinson, L. H. Rombach, W. L. Truett, US Patent 2932630, 1960; W. L. Truett, D. R. Johnson, I. M. Robinson, B. A. Montague, J. Am. Chem. Soc. 1960, 82, 2337.
4. In fact there is earlier evidence for that the discovery of that reaction in polymer chemistry (ROMP): A. W. Anderson, N. G. Merckling, US Patent 2721189, 1955; I. M. Robinson, L. H. Rombach, W. L. Truett, US Patent 2932630, 1960; W. L. Truett, D. R. Johnson, I. M. Robinson, B. A. Montague, J. Am. Chem. Soc. 1960, 82, 2337.
5. In fact there is earlier evidence for that the discovery of that reaction in polymer chemistry (ROMP): A. W. Anderson, N. G. Merckling, US Patent 2721189, 1955; I. M. Robinson, L. H. Rombach, W. L. Truett, US Patent 2932630, 1960; W. L. Truett, D. R. Johnson, I. M. Robinson, B. A. Montague, J. Am. Chem. Soc. 1960, 82, 2337.
6. For a comprehensive review: In Olefin Metathesis and Metathesis Polymerization (Eds. K. J. Ivin, J. C. Mol), Academic Press, San Diego, 1997.
7. J.-L. Hérisson, Y. Chauvin, Makromol. Chem. 1971, 141, 161.
8. a) W. R. Kroll, G. Doyle, J. Chem. Soc. Chem. Commun. 1971, 839;
9. b) C. P. Casey, T. J. Burkhardt, J. Am. Chem. Soc. 1973, 95, 5833;
10. c) T. J. Katz, S. J. Lee, Tetrahedron Lett. 1976, 4247;
11. d) For a review on alkylidene complexes, see: R. R. Schrock, Chem. Rev. 2002, 102, 145.
12. Review on olefin metathesis for homogeneous catalysis: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18; b) R. R. Schrock, A. H. Hoveyda, Chem. Eur. J. 2001, 7, 945.
13. Review on olefin metathesis for homogeneous catalysis: a) T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18; b) R. R. Schrock, A. H. Hoveyda, Chem. Eur. J. 2001, 7, 945.
14. a) E. J. Howman, L. Turner, NL Patent, 6605328, 1966;
15. b) J. Cosyns, J. Chodorge, D. Commereuc, B. Torck, Hydrocarbon Process, 1998, 60.
16. a) E. Verkuijlen, F. Kapteijn, J. C. Mol, C. Boelhouwer, J. Chem. Soc. Chem. Commun. 1977, 198;
17. b) M. Sibeijn, J. C. Mol, Appl. Catal. 1991, 67, 279;
18. c) J. C. Mol, Green Chem. 2002, 4, 5.
19. a) F. Kapteijn, H. L. G. Bredt, E. Homburg, J. C. Mol, Ind. Eng. Chem. Prod. Res. Dev. 1981, 20, 457;
20. b) Y. Chauvin, D. Commereuc, J. Chem. Soc. Chem. Commun. 1992, 462.
21. J. C. Mol, Catal. Today 1999, 51, 289.
22. C. Copéret, M. Chabanas, R. Petroff Saint-Arroman, J.-M. Basset, Angew. Chem. 2003, 115, 164; Angew. Chem. Int. Ed. 2003, 42, 156.
23. C. Copéret, M. Chabanas, R. Petroff Saint-Arroman, J.-M. Basset, Angew. Chem. 2003, 115, 164; Angew. Chem. Int. Ed. 2003, 42, 156.
24. a) M. Chabanas, A. Baudouin, C. Copéret, J.-M. Basset, J. Am. Chem. Soc. 2001, 123, 2062;
25. b) A. Lesage, L. Emsley, M. Chabanas, C. Copéret, J.-M. Basset, Angew. Chem. 2002, 114, 4717; Angew. Chem. Int. Ed. 2002, 41, 4535;
26. b) A. Lesage, L. Emsley, M. Chabanas, C. Copéret, J.-M. Basset, Angew. Chem. 2002, 114, 4717; Angew. Chem. Int. Ed. 2002, 41, 4535;
27. c) M. Chabanas, C. Copéret, A. Baudouin, J.-M. Basset, W. Lukens, A. Lesage, L. Emsley, J. Am. Chem. Soc. 2003, 125, 492.
28. The activity of rhenium oxides supported on silica is usually poor under 120°C. For some examples, see: a) A. W. Aldag, C. J. Lin, A. Clark, Recl. Trav. Chim. Pays-Bas, 1977, 96, M27; b) N. Tsuda, A. Fujimori, J. Catal. 1981, 69, 410; c) L. G. Duquette, R. C. Cieslinski, C. H. Jung, P. E. Garrou, J. Catal. 1984, 90, 362; d) P. S. Kirlin, B. C. Gates, J. Chem. Soc. Chem. Commun. 1985, 277; e) R. M. Edreva-Kardjieva, A. A. Andreev, J. Catal. 1986, 97, 321.
29. The activity of rhenium oxides supported on silica is usually poor under 120°C. For some examples, see: a) A. W. Aldag, C. J. Lin, A. Clark, Recl. Trav. Chim. Pays-Bas, 1977, 96, M27; b) N. Tsuda, A. Fujimori, J. Catal. 1981, 69, 410; c) L. G. Duquette, R. C. Cieslinski, C. H. Jung, P. E. Garrou, J. Catal. 1984, 90, 362; d) P. S. Kirlin, B. C. Gates, J. Chem. Soc. Chem. Commun. 1985, 277; e) R. M. Edreva-Kardjieva, A. A. Andreev, J. Catal. 1986, 97, 321.
30. The activity of rhenium oxides supported on silica is usually poor under 120°C. For some examples, see: a) A. W. Aldag, C. J. Lin, A. Clark, Recl. Trav. Chim. Pays-Bas, 1977, 96, M27; b) N. Tsuda, A. Fujimori, J. Catal. 1981, 69, 410; c) L. G. Duquette, R. C. Cieslinski, C. H. Jung, P. E. Garrou, J. Catal. 1984, 90, 362; d) P. S. Kirlin, B. C. Gates, J. Chem. Soc. Chem. Commun. 1985, 277; e) R. M. Edreva-Kardjieva, A. A. Andreev, J. Catal. 1986, 97, 321.
31. The activity of rhenium oxides supported on silica is usually poor under 120°C. For some examples, see: a) A. W. Aldag, C. J. Lin, A. Clark, Recl. Trav. Chim. Pays-Bas, 1977, 96, M27; b) N. Tsuda, A. Fujimori, J. Catal. 1981, 69, 410; c) L. G. Duquette, R. C. Cieslinski, C. H. Jung, P. E. Garrou, J. Catal. 1984, 90, 362; d) P. S. Kirlin, B. C. Gates, J. Chem. Soc. Chem. Commun. 1985, 277; e) R. M. Edreva-Kardjieva, A. A. Andreev, J. Catal. 1986, 97, 321.
32. The activity of rhenium oxides supported on silica is usually poor under 120°C. For some examples, see: a) A. W. Aldag, C. J. Lin, A. Clark, Recl. Trav. Chim. Pays-Bas, 1977, 96, M27; b) N. Tsuda, A. Fujimori, J. Catal. 1981, 69, 410; c) L. G. Duquette, R. C. Cieslinski, C. H. Jung, P. E. Garrou, J. Catal. 1984, 90, 362; d) P. S. Kirlin, B. C. Gates, J. Chem. Soc. Chem. Commun. 1985, 277; e) R. M. Edreva-Kardjieva, A. A. Andreev, J. Catal. 1986, 97, 321.
33. a) J. L. Bilhou, J.-M. Basset, R. Mutin, W. F. Graydon, J. Chem. Soc. Chem. Commun. 1976, 23, 970;
34. b) J. L. Bilhou, J.-M. Basset, R. Mutin, W. F. Graydon, J. Am. Chem. Soc. 1977, 99, 4083.
35. a) R. Nakamura, H. Iida, E. Echigoya, Chem. Lett. 1972, 273;
36. b) W. von Siegfried, G. Puetz, Chem.-Ztg. 1988, 15;
37. c) T. Kawai, M. Furuki, T. Ishikawa, J. Mol. Catal. 1994, 90, 1.
38. For examples of Re oxide on other supports, see also: a) W. A. Herrmann, W. Wagner, U. N. Flessner, U. Volkhardt, H. Komber, Angew. Chem. 1991, 103, 1704; Angew. Chem. Int. Ed. Engl. 1991, 30, 1636; b) R. Buffon, A. Auroux, F. Lefebvre, M. Leconte, A. Choplin, J.-M. Basset, W. A. Herrmann, J. Mol. Catal. 1992, 76, 287-95; c) R. Buffon, A. Choplin, M. Leconte, J.-M. Basset, R. Touroude, W. A. Herrmann, J. Mol. Catal. 1992, 72, L7-10.
39. For examples of Re oxide on other supports, see also: a) W. A. Herrmann, W. Wagner, U. N. Flessner, U. Volkhardt, H. Komber, Angew. Chem. 1991, 103, 1704; Angew. Chem. Int. Ed. Engl. 1991, 30, 1636; b) R. Buffon, A. Auroux, F. Lefebvre, M. Leconte, A. Choplin, J.-M. Basset, W. A. Herrmann, J. Mol. Catal. 1992, 76, 287-95; c) R. Buffon, A. Choplin, M. Leconte, J.-M. Basset, R. Touroude, W. A. Herrmann, J. Mol. Catal. 1992, 72, L7-10.
40. For examples of Re oxide on other supports, see also: a) W. A. Herrmann, W. Wagner, U. N. Flessner, U. Volkhardt, H. Komber, Angew. Chem. 1991, 103, 1704; Angew. Chem. Int. Ed. Engl. 1991, 30, 1636; b) R. Buffon, A. Auroux, F. Lefebvre, M. Leconte, A. Choplin, J.-M. Basset, W. A. Herrmann, J. Mol. Catal. 1992, 76, 287-95; c) R. Buffon, A. Choplin, M. Leconte, J.-M. Basset, R. Touroude, W. A. Herrmann, J. Mol. Catal. 1992, 72, L7-10.
41. For examples of Re oxide on other supports, see also: a) W. A. Herrmann, W. Wagner, U. N. Flessner, U. Volkhardt, H. Komber, Angew. Chem. 1991, 103, 1704; Angew. Chem. Int. Ed. Engl. 1991, 30, 1636; b) R. Buffon, A. Auroux, F. Lefebvre, M. Leconte, A. Choplin, J.-M. Basset, W. A. Herrmann, J. Mol. Catal. 1992, 76, 287-95; c) R. Buffon, A. Choplin, M. Leconte, J.-M. Basset, R. Touroude, W. A. Herrmann, J. Mol. Catal. 1992, 72, L7-10.
42. 0 Re alkylidene complexes as homogenous catalyst precursors for olefin metathesis, see: a) R. Toreki, R. R. Schrock, J. Am. Chem. Soc. 1990, 112, 2448; b) R. Toreki, R. R. Schrock, M. G. Vale, J. Am. Chem. Soc. 1991, 113, 3610; c) M. H. Schofield, R. R. Schrock, L. Y. Park, Organometallics 1991, 10, 1844; d) R. Toreki, G. A. Vaughan, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1993, 115, 127; e) G. A. Vaughan, R. Toreki, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1993, 115, 2980; f) A. M. LaPointe, R. R. Schrock, Organometallics 1995, 14, 1875; g) B. T. Flatt, R. H. Grubbs, R. L. Blanski, J. C. Calabrese, J. Feldman, Organometallics 1994, 13, 2728; h) D. Commereuc, J. Chem. Soc. Chem. Commun. 1995, 791.
43. 0 Re alkylidene complexes as homogenous catalyst precursors for olefin metathesis, see: a) R. Toreki, R. R. Schrock, J. Am. Chem. Soc. 1990, 112, 2448; b) R. Toreki, R. R. Schrock, M. G. Vale, J. Am. Chem. Soc. 1991, 113, 3610; c) M. H. Schofield, R. R. Schrock, L. Y. Park, Organometallics 1991, 10, 1844; d) R. Toreki, G. A. Vaughan, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1993, 115, 127; e) G. A. Vaughan, R. Toreki, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1993, 115, 2980; f) A. M. LaPointe, R. R. Schrock, Organometallics 1995, 14, 1875; g) B. T. Flatt, R. H. Grubbs, R. L. Blanski, J. C. Calabrese, J. Feldman, Organometallics 1994, 13, 2728; h) D. Commereuc, J. Chem. Soc. Chem. Commun. 1995, 791.
44. 0 Re alkylidene complexes as homogenous catalyst precursors for olefin metathesis, see: a) R. Toreki, R. R. Schrock, J. Am. Chem. Soc. 1990, 112, 2448; b) R. Toreki, R. R. Schrock, M. G. Vale, J. Am. Chem. Soc. 1991, 113, 3610; c) M. H. Schofield, R. R. Schrock, L. Y. Park, Organometallics 1991, 10, 1844; d) R. Toreki, G. A. Vaughan, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1993, 115, 127; e) G. A. Vaughan, R. Toreki, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1993, 115, 2980; f) A. M. LaPointe, R. R. Schrock, Organometallics 1995, 14, 1875; g) B. T. Flatt, R. H. Grubbs, R. L. Blanski, J. C. Calabrese, J. Feldman, Organometallics 1994, 13, 2728; h) D. Commereuc, J. Chem. Soc. Chem. Commun. 1995, 791.
45. 0 Re alkylidene complexes as homogenous catalyst precursors for olefin metathesis, see: a) R. Toreki, R. R. Schrock, J. Am. Chem. Soc. 1990, 112, 2448; b) R. Toreki, R. R. Schrock, M. G. Vale, J. Am. Chem. Soc. 1991, 113, 3610; c) M. H. Schofield, R. R. Schrock, L. Y. Park, Organometallics 1991, 10, 1844; d) R. Toreki, G. A. Vaughan, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1993, 115, 127; e) G. A. Vaughan, R. Toreki, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1993, 115, 2980; f) A. M. LaPointe, R. R. Schrock, Organometallics 1995, 14, 1875; g) B. T. Flatt, R. H. Grubbs, R. L. Blanski, J. C. Calabrese, J. Feldman, Organometallics 1994, 13, 2728; h) D. Commereuc, J. Chem. Soc. Chem. Commun. 1995, 791.
46. 0 Re alkylidene complexes as homogenous catalyst precursors for olefin metathesis, see: a) R. Toreki, R. R. Schrock, J. Am. Chem. Soc. 1990, 112, 2448; b) R. Toreki, R. R. Schrock, M. G. Vale, J. Am. Chem. Soc. 1991, 113, 3610; c) M. H. Schofield, R. R. Schrock, L. Y. Park, Organometallics 1991, 10, 1844; d) R. Toreki, G. A. Vaughan, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1993, 115, 127; e) G. A. Vaughan, R. Toreki, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1993, 115, 2980; f) A. M. LaPointe, R. R. Schrock, Organometallics 1995, 14, 1875; g) B. T. Flatt, R. H. Grubbs, R. L. Blanski, J. C. Calabrese, J. Feldman, Organometallics 1994, 13, 2728; h) D. Commereuc, J. Chem. Soc. Chem. Commun. 1995, 791.
47. 0 Re alkylidene complexes as homogenous catalyst precursors for olefin metathesis, see: a) R. Toreki, R. R. Schrock, J. Am. Chem. Soc. 1990, 112, 2448; b) R. Toreki, R. R. Schrock, M. G. Vale, J. Am. Chem. Soc. 1991, 113, 3610; c) M. H. Schofield, R. R. Schrock, L. Y. Park, Organometallics 1991, 10, 1844; d) R. Toreki, G. A. Vaughan, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1993, 115, 127; e) G. A. Vaughan, R. Toreki, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1993, 115, 2980; f) A. M. LaPointe, R. R. Schrock, Organometallics 1995, 14, 1875; g) B. T. Flatt, R. H. Grubbs, R. L. Blanski, J. C. Calabrese, J. Feldman, Organometallics 1994, 13, 2728; h) D. Commereuc, J. Chem. Soc. Chem. Commun. 1995, 791.
48. 0 Re alkylidene complexes as homogenous catalyst precursors for olefin metathesis, see: a) R. Toreki, R. R. Schrock, J. Am. Chem. Soc. 1990, 112, 2448; b) R. Toreki, R. R. Schrock, M. G. Vale, J. Am. Chem. Soc. 1991, 113, 3610; c) M. H. Schofield, R. R. Schrock, L. Y. Park, Organometallics 1991, 10, 1844; d) R. Toreki, G. A. Vaughan, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1993, 115, 127; e) G. A. Vaughan, R. Toreki, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1993, 115, 2980; f) A. M. LaPointe, R. R. Schrock, Organometallics 1995, 14, 1875; g) B. T. Flatt, R. H. Grubbs, R. L. Blanski, J. C. Calabrese, J. Feldman, Organometallics 1994, 13, 2728; h) D. Commereuc, J. Chem. Soc. Chem. Commun. 1995, 791.
49. 0 Re alkylidene complexes as homogenous catalyst precursors for olefin metathesis, see: a) R. Toreki, R. R. Schrock, J. Am. Chem. Soc. 1990, 112, 2448; b) R. Toreki, R. R. Schrock, M. G. Vale, J. Am. Chem. Soc. 1991, 113, 3610; c) M. H. Schofield, R. R. Schrock, L. Y. Park, Organometallics 1991, 10, 1844; d) R. Toreki, G. A. Vaughan, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1993, 115, 127; e) G. A. Vaughan, R. Toreki, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1993, 115, 2980; f) A. M. LaPointe, R. R. Schrock, Organometallics 1995, 14, 1875; g) B. T. Flatt, R. H. Grubbs, R. L. Blanski, J. C. Calabrese, J. Feldman, Organometallics 1994, 13, 2728; h) D. Commereuc, J. Chem. Soc. Chem. Commun. 1995, 791.
50. M. B. Dinger, J. C. Mol, Adv. Synth. Catal. 2002, 344, 671.