Catalytic functionalization of hydrocarbons by σ-bond-metathesis chemistry: Dehydrosilylation of methane with a scandium catalyst

Angewandte Chemie - International Edition

Volumn 42, Issue 7, 2003, Pages 803-805

  Sadow, Aaron D ^a   Tilley, T Don ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

C H activation; Homogeneous catalysis; Methane; Scandium; Silanes

Indexed keywords

CATALYSIS; CATALYSTS; CHEMICAL BONDS;

DEHYDROSILYLATION;

HYDROCARBONS;

BENZENE; HYDROCARBON; METHANE; SCANDIUM; SILANE DERIVATIVE; SILICON DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; COMPLEX FORMATION; REACTION ANALYSIS; RING CLOSING METATHESIS; SILYLATION;

EID: 0037450135     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390213     Document Type: Article

References (39)

1. a) J. A. Labinger, J. E. Bercaw, Nature 2002, 417, 507;
2. b) R. H. Crabtree, J. Chem. Soc. Dalton Trans. 2001, 2437;
3. c) A. Sen, Acc. Chem. Res. 1998, 31, 550;
4. d) S. S. Stahl, J. A. Labinger, J. E. Bercaw, Angew. Chem. 1998, 110, 2298; Angew. Chem. Int. Ed. 1998, 37, 2180;
5. d) S. S. Stahl, J. A. Labinger, J. E. Bercaw, Angew. Chem. 1998, 110, 2298; Angew. Chem. Int. Ed. 1998, 37, 2180;
6. e) A. E. Shilov, G. B. Shul'pin, Chem. Rev. 1997, 97, 2879;
7. f) B. A. Arndtsen, R. G. Bergman, T. A. Mobley, T. H. Peterson, Acc. Chem. Res. 1995, 28, 154.
8. Some recent representative examples of catalytic hydrocarbon functionalizations: a) H. Chen, S. Schlecht, T. C. Semple, J. F. Hartwig, Science 2000, 287, 1995; b) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, M. R. Smith, Science 2002, 295, 305; c) C. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura, Y. Fujiwara, Science 2000, 287, 1992; d) F. Liu, E. B. Pak, B. Singh, C. M. Jensen, A. S. Goldman, J. Am. Chem. Soc. 1999, 121, 4086.
9. Some recent representative examples of catalytic hydrocarbon functionalizations: a) H. Chen, S. Schlecht, T. C. Semple, J. F. Hartwig, Science 2000, 287, 1995; b) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, M. R. Smith, Science 2002, 295, 305; c) C. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura, Y. Fujiwara, Science 2000, 287, 1992; d) F. Liu, E. B. Pak, B. Singh, C. M. Jensen, A. S. Goldman, J. Am. Chem. Soc. 1999, 121, 4086.
10. Some recent representative examples of catalytic hydrocarbon functionalizations: a) H. Chen, S. Schlecht, T. C. Semple, J. F. Hartwig, Science 2000, 287, 1995; b) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, M. R. Smith, Science 2002, 295, 305; c) C. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura, Y. Fujiwara, Science 2000, 287, 1992; d) F. Liu, E. B. Pak, B. Singh, C. M. Jensen, A. S. Goldman, J. Am. Chem. Soc. 1999, 121, 4086.
11. Some recent representative examples of catalytic hydrocarbon functionalizations: a) H. Chen, S. Schlecht, T. C. Semple, J. F. Hartwig, Science 2000, 287, 1995; b) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, M. R. Smith, Science 2002, 295, 305; c) C. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura, Y. Fujiwara, Science 2000, 287, 1992; d) F. Liu, E. B. Pak, B. Singh, C. M. Jensen, A. S. Goldman, J. Am. Chem. Soc. 1999, 121, 4086.
12. R. A. Periana, D. J. Taube, S. Gamble, H. Taube, T. Satoh, H. Fujii, Science 1998, 280, 560.
13. a) G. V. Nizova, G. Suss-Fink, G. B. Shul'pin, Chem. Commun. 1997, 397;
14. b) M. N. Vargaftik, I. P. Stolarov, I. I. Moiseev, J. Chem. Soc. Chem. Commun. 1990, 1049;
15. c) M. Merkx, D. A. Kopp, M. H. Sazinsky, J. L. Blazyk, J. Müller, S. J. Lippard, Angew. Chem. 2001, 113, 2860; Angew. Chem. Int. Ed. 2001, 40, 2782.
16. c) M. Merkx, D. A. Kopp, M. H. Sazinsky, J. L. Blazyk, J. Müller, S. J. Lippard, Angew. Chem. 2001, 113, 2860; Angew. Chem. Int. Ed. 2001, 40, 2782.
17. R. H. Crabtree, Chem. Rev. 1995, 95, 987, and references therein.
18. a) P. L. Watson, G. W. Parshall, Acc. Chem. Res. 1985, 18, 51;
19. b) M. E. Thompson, S. M. Baxter, A. R. Bulls, B. J. Burger, M. C. Nolan, B. D. Santarsiero, W. P. Schaefer, J. E. Bercaw, J. Am. Chem. Soc. 1987, 109, 203;
20. c) C. M. Fendrick, T. J. Marks, J. Am. Chem. Soc. 1986, 108, 425.
21. W. E. Piers, P. J. Shapiro, E. E. Bunel, J. E. Bercaw, Synlett 1990, 74.
22. a) P.-F. Fu, L. Brard, Y. Li, T. J. Marks, J. Am. Chem. Soc. 1995, 117, 7157, and references therein;
23. b) T. I. Gountchev, T. D. Tilley, Organometallics 1999, 18, 5661;
24. c) G. A. Molander, M. Julius, J. Am. Chem. Soc. 1995, 117, 4415;
25. d) A. K. Dash, I. Gourevich, J. Q. Wang, J. Wang, M. Kapon, M. S. Eisen, Organometallics 2001, 20, 5084.
26. a) C. T. Aitken, J. F. Harrod, E. Samuel, J. Am. Chem. Soc. 1986, 108, 4059;
27. b) J. Y. Corey, X.-H. Zhu, T. C. Bedard, L. D. Lange, Organometallics, 1991, 10, 115;
28. c) T. D. Tilley, Acc. Chem. Res. 1993, 26, 22.
29. a) H.-G. Woo, J. F. Walzer, T. D. Tilley, J. Am. Chem. Soc. 1992, 114, 7047;
30. b) G. L. Casty, C. G. Lugmair, N. S. Radu, T. D. Tilley, J. F. Walzer, D. Zargarian, Organometallics 1997, 16, 8;
31. c) N. S. Radu, T. D. Tilley, J. Am. Chem. Soc. 1992, 114, 8293.
32. A. D. Sadow, T. D. Tilley, J. Am. Chem. Soc. 2002, 124, 6814.
33. M. E. Thompson, J. E. Bercaw, Pure Appl. Chem. 1984, 56, 1.
34. A. Z. Voskoboynikov, I. N. Parshina, A. K. Shestakova, K. P. Butin, I. P. Beletskaya, L. G. Kuz'mina, J. A. K. Howard, Organometallics 1997, 16, 4041.
35. N. S. Radu, T. D. Tilley, J. Am. Chem. Soc. 1995, 117, 5863.
36. Reactions of 1 with organosilanes are highly sensitive to the nature of substituents at silicon; A. D. Sadow, T. D. Tilley, unpublished results.
37. T. Imori, V. Lu, H. Cai, T. D. Tilley, J. Am. Chem. Soc. 1995, 117, 9931.
38. R. F. Jordan, D. F. Taylor, J. Am. Chem. Soc. 1989, 111, 778.
39. A. K. Dash, J. Q. Wang, M. S. Eisen, Organometallics 1999, 18, 4727.