Highly efficient hydrosilylation of alkenes by organoyttrium catalysts with sterically demanding amidinate and guanidinate ligands

Organometallics

Volumn 27, Issue 13, 2008, Pages 3131-3135

  Ge, Shaozhong ^a   Meetsma, Auke ^a   Hessen, Bart ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CHELATION; CHEMICAL REACTIONS; HYDROCARBONS; HYDROSILYLATION; OLEFINS;

AMIDINATE; GUANIDINATE; HIGHLY EFFICIENT; STERICALLY DEMANDING;

CATALYSIS;

EID: 47949121369     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800032g     Document Type: Article

References (44)

1. Marciniec, B.; Gulinski, J.; Urbaniac, W.; Kornetka, Z. W. Comprehensive Handbook on Hydrosilylation; Pergamon: Oxford, U.K., 1992.
2. Lewis, L. N.; Stein, J.; Gao, Y.; Colborn, R. E.; Hutchins, G. Platinum Met. Rev. 1997, 21, 66.
3. (a) Speier, J. L. Adv. Organomet. Chem. 1979, 17, 407.
4. (b) Speier, J. L.; Webster, J. A.; Barnes, G. H. J. Am. Chem. Soc. 1956, 79, 974.
5. (c) Karstedt, B. D. U.S. Patent 3,715,334, 1973.
6. (d) Markó, I. E.; Stérin, S.; Buisine, O.; Mignani, G.; Brandlard, P.; Tinant, B.; Delcercq, J.-P. Science 2002, 298, 204.
7. (e) Markó, I. E.; Michaud, G.; Berthon-Gelloz, G.; Buisine, O.; Sterin, S. Adv. Synth. Catal. 2004, 346, 1429.
8. (f) Buisine, O.; Berthon-Gelloz, G.; Brière, J.-F.; Stérin, S.; Mignani, G.; Brandlard, P.; Tinant, B.; Delcercq, J.-P.; Markó, I. E. Chem. Commun. 2005, 3856.
9. West, R. Comprehensive Organometallic Chemistry II; Elsevier: Amsterdam, 1995; Vol. 2, p 77.
10. (a) Harrod, J. F.; Yun. S. S. Organometallics 1987, 6, 1381.
11. (b) Kesti, M. R.; Waymouth. R. M. Organometallics 1992, 11, 1095.
12. Dash. A. K.; Gourevich, I.; Wang, J. Q.; Wang. J.: Kapon, M.; Eisen, M. S. Organometallics 2001, 20, 5084.
13. (a) Sakakura, Y.; Lautenschlager, H. J.; Tanaka, M. J. J. Chem. Soc., Chem. Commun. 1991, 40.
14. (b) Molander, G. A.; Julius, M. J. Org. Chem. 1992, 57, 6347.
15. (c) Yu, P. F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157.
16. (d) Molander, G. A.; Retsch, W. H. J. Am. Chem. Soc. 1997, 119, 8817.
17. (e) Molander, G. A.; Dowdy, E. D.; Noll, B. C. Organometallics 1997, 17, 3754.
18. (f) Takaki, K.; Sonoda, K.; Kousaka, T.; Koshoji, G.; Shishido, T.; Takehira, K. Tetrahedron Lett. 2001, 42, 9211.
19. (g) Hou, Z.; Zhang, Y.; Tardif, O.; Wakatsuki, Y. J. Am. Chem. Soc. 2001, 123, 9216.
20. (h) Voskoboynikov, A. Z.; Shestakova, A. K.; Beletskaya, I. P. Organometallics 2001, 20, 2794.
21. (i) Trifonov, A. A.; Spaniol, T. P.; Okuda, J. Organometallics 2001, 20, 4869.
22. (j) Tardif, O.; Nishiura, M; Hou, Z. Tetrahedron 2003, 59, 10525.
23. (k) Horino, Y.; Livinghouse, T. Organometallics 2004, 23, 12.
24. (l) Robert, D.; Trifonov, A. A.; Voth, P.; Okuda, J. J. Organomet. Chem. 2006, 697, 4393.
25. (a) Barker, J.; Kilner, M. Coord. Chem. Rev. 1994, 133, 219.
26. (b) Edelmann, F. T. Coord. Chem. Rev. 1994, 137, 403.
27. (c) Bailey, P. J.; Pace, S. Coord. Chem. Rev. 2001, 214, 91.
28. (d) Kissounko, A.; Zabalov, M. V.; Brusova, G. P.; Lemenovskii, D. A. Russ. Chem. Rev. 2006, 75, 351-374.
29. (a) Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Chem. Commun. 2003, 522.
30. (b) Bambirra, S.; Bouwkamp, M. W.; Meetsma, A.; Hessen, B. J. Am. Chem. Soc. 2004, 126, 9182.
31. (c) Bambirra, S.; Tsurugi, H.; Van Leusen, D.; Hessen, B. Dalton Trans. 2006, 1157.
32. (d) Bambirra, S.; Meetsma, A.; Hessen, B. Organometallics 2006, 25, 3454.
33. (e) Bambirra, S.; Otten, E.; Van Leusen, D.; Meetsma, A.; Hessen, B. Z. Anorg. Allg. Chem. 2006, 632, 1950.
34. (a) Trifonov, A. A.; Lyubov, D. M.; Fukin, G. K.; Baranov, E. V.; Kurskii, Y. A. Organometallics 2006, 25, 3935.
35. (b) Lyubov. D. M.; Fukin, G. K.; Trifonov, A. A. Inorg. Chem. 2007, 46, 11450.
36. Neumann, W.; Bayer, O.; Unterstenhoefer, G.; Grewe, F. Ger. Offen. DE 1192453, 1965.
37. 3 was observed, a clear indication of smooth Y-H formation.
38. Hultzsch. K. C.: Voth, P.; Beckerle. K.; Spaniol, T. P.; Okuda, J. Organometallics 2000, 19, 228.
39. Seebach, D.; Corey, E. J. J. Org. Chem. 1975, 40, 231.
40. Cloux, R.; Schlosser, M. Helv. Chim. Acta 1984, 67, 1470.
41. Sheldrick, G. M. SADABS Version 2, Empirical Absorption Correction Program; University of Göttingen, Göttingen, Germany, 2000.
42. Beurskens, P. T.; Beurskens, G.; De Gelder, R.; Garcia-Granda, S.; Gould, R. O.; Israel, R.; Smits, J. M. M. The DIRDIF-99 Program System; Crystallography Laboratory, University of Nijmegen, Nijmegen, The Netherlands, 1999.
43. Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures; University of Göttingen, Göttingen, Germany, 1997.
44. Spek, A. L. PLATON, Program for the Automated Analysis of Molecular Geometry, April 2000 Version; University of Utrecht, Utrecht, The Netherlands.