Experimental and computational studies of the ruthenium-catalyzed hydrosilylation of alkynes: Mechanistic insights into the regio- and stereoselective formation of vinylsilanes

Organometallics

Volumn 33, Issue 23, 2014, Pages 6937-6944

  Gao, Ruili ^a   Pahls, Dale R ^b   Cundari, Thomas R ^b   Yi, Chae S ^a  

^a Marquette University   (United States)

^b UNIVERSITY OF NORTH TEXAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROSILYLATION; ISOMERIZATION; ISOMERS; PHOSPHORUS COMPOUNDS; RUTHENIUM; RUTHENIUM COMPOUNDS; STEREOSELECTIVITY;

COMPUTATIONAL DATA; COMPUTATIONAL STUDIES; EMPIRICAL RATE LAW; HYDROSILYLATION REACTION; INHIBITION KINETICS; RUTHENIUM HYDRIDE COMPLEX; STEREOSELECTIVE FORMATION; STERICALLY DEMANDING;

HYDROCARBONS;

EID: 84916204746     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om501019j     Document Type: Article

References (50)

1. Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375
2. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063
3. Pouget, E.; Tonnar, J.; Lucas, P.; Lacroix-Desmazes, P.; Ganachaud, F.; Boutevin, B. Chem. Rev. 2010, 110, 1233
4. Ojima, I.; Li, Z.; Zhu, J. In The Chemistry of Organic Silicon Compounds; Rappoport, S.; Apeloig, Y., Eds.; Wiley: New York, 1998.
5. Reichl, J.; Berry, D. H. Adv. Organomet. Chem. 1998, 43, 197
6. Marciniec, B. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B.; Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Vol. 1.
7. Marciniec, B. In Hydrosilylation: A Comprehensive Review on Recent Advances;; Matisons, J., Ed.; Springer: New York, 2009; pp 53-123.
8. Aneetha, H.; Wu, W.; Verkade, J. G. Organometallics 2005, 24, 2590
9. Poyatos, M.; Maisse-Francois, A.; Bellemin-Laponnaz, S.; Gade, L. H. Organometallics 2006, 25, 2634
10. Berthon-Gelloz, G.; Schumers, J. M.; Bo, G. D.; Markó, I. E. J. Org. Chem. 2008, 73, 4190
11. Blug, M.; Le Goff, X.-F.; Mézeiles, N.; Le Floch, P. Organometallics 2009, 28, 2360
12. Cano, R.; Yus, M.; Ramón, D. J. ACS Catal. 2012, 2, 1070
13. Alonso, F.; Buitrago, R.; Moglie, Y.; Sepúlveda-Escribano, A.; Yus, M. Organometallics 2012, 31, 2336
14. Takeuchi, R.; Tanouchi, N. Chem. Commun. 1993, 1319
15. Takeuchi, R.; Tanouchi, N. Perkin Trans. 1994, 2909
16. Takeuchi, R.; Nitta, S.; Watanabe, D. Chem. Commun. 1994, 1777
17. Trost, B. M.; Ball, Z. T.; Jöge, T. J. Am. Chem. Soc. 2002, 124, 7922
18. Trost, B. M.; Ball, Z. T. J. Am. Chem. Soc. 2003, 125, 30
19. Trost, B. M.; Ball, Z. T. J. Am. Chem. Soc. 2004, 126, 13942
20. Trost, B. M.; Ball, Z. T. J. Am. Chem. Soc. 2005, 127, 17644
21. Trost, B. M.; Ball, Z. T.; Laemmerhold, K. M. J. Am. Chem. Soc. 2005, 127, 10028
22. Tanke, R. S.; Crabtree, R. H. J. Am. Chem. Soc. 1990, 112, 7984
23. Na, Y.; Chang, S. Org. Lett. 2000, 2, 1887
24. Mori, A.; Takahisa, E.; Yamamura, Y.; Kato, T.; Mudalige, A. P.; Kajiro, H.; Hirabayashi, K.; Nishihara, Y.; Hiyama, T. Organometallics 2004, 23, 1755
25. Liu, Y.; Yamazaki, S.; Yamabe, S. J. Org. Chem. 2005, 70, 556
26. Nagao, M.; Asano, K.; Umeda, K.; Katayama, H.; Ozawa, F. J. Org. Chem. 2005, 70, 10511
27. Iglesias, M.; Pérez-Nicolás, M.; Sanz Miguel, P. J.; Polo, V.; Fernández-Alvarez, F. J.; Pérez-Torrente, J. J.; Oro, L. A. Chem. Commun. 2012, 48, 9480
28. Kawasaki, Y.; Ishikawa, Y.; Igawa, K.; Tomooka, K. J. Am. Chem. Soc. 2011, 133, 20712
29. Rooke, D. A.; Ferreira, E. M. Angew. Chem., Int. Ed. 2012, 51, 3225
30. Sumida, Y.; Kato, T.; Yoshida, S.; Hosoya, T. Org. Lett. 2012, 14, 1552
31. Rooke, D. A.; Ferreira, E. M. Org. Lett. 2012, 14, 3328
32. Hamze, A.; Provot, O.; Alami, M.; Brion, J.-D. Org. Lett. 2005, 7, 5625
33. Yi, C. S. J. Organomet. Chem. 2011, 696, 76 and references cited therein
34. Yi, C. S.; He, Z.; Lee, D. W.; Rheingold, A. L.; Lam, K.-C. Organometallics 2000, 19, 2036
35. Yi, C. S.; Gao, R. Organometallics 2009, 28, 6585
36. Fernandez, M. J.; Oro, L. A.; Manzano, B. R. J. Mol. Catal. 1988, 45, 7
37. Faller, J. W.; DAlliessi, D. G. Organometallics 2002, 21, 1743
38. Vincent, C.; Viciano, M.; Mas-Marzá, E.; Sanaú, M. Organometallics 2006, 25, 3713
39. Segel, I. H. Enzyme Kinetics; Wiley: New York, 1975.
40. Yi, C. S.; Lee, D. W.; Chen, Y. Organometallics 1999, 18, 2043
41. Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024
42. Becke, A. D. J. Chem. Phys. 1993, 98, 1372
43. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
44. Stevens, W. J.; Basch, H.; Krauss, M. J. Chem. Phys. 1984, 81, 6026
45. Stevens, W. J.; Krauss, M.; Basch, H.; Jasien, P. G. Can. J. Chem. 1992, 70, 612
46. Tolman, C. A. J. Am. Chem. Soc. 1970, 92, 2956
47. Tolman, C. A. Chem. Rev. 1977, 77, 313
48. Chung, L. W.; Wu, Y.-D.; Trost, B. M.; Ball, Z. T. J. Am. Chem. Soc. 2003, 125, 11578
49. Sridevi, V. S.; Fan, W. Y.; Leong, W. K. Organometallics 2007, 26, 1157
50. Yang, Y.-F.; Chung, L. W.; Zhang, X.; Houk, K. N.; Wu, Y.-D. J. Org. Chem. 2014, 79, 8856