Electrospray ionization mass spectrometry studies on the mechanism of hydrosilylation of terminal alkynes using an N-heterocyclic carbene complex of iridium, allow detection/characterization of all reaction intermediates

Organometallics

Volumn 25, Issue 15, 2006, Pages 3713-3720

  Vicent, Cristian ^a   Viciano, Monica ^a   Mas Marzá, Elena ^a   Sanaú, Mercedes ^b   Peris, Eduardo ^a  

^a UNIVERSITAT JAUME I   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; HYDROGEN INORGANIC COMPOUNDS; IRIDIUM COMPOUNDS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; ORGANOMETALLICS; REACTION KINETICS;

DEHYDROGENATIVE SILYLATION PRODUCTS; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; HYDROSILYLATION; PHENYLACETYLENE;

HYDROCARBONS;

EID: 33746338244     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0602308     Document Type: Article

References (64)

1. Ojima, I. The Chemistry of Organic Silicon Compounds; Wiley: New York, 1989; p 1479.
2. Ojima, I.; Li, Z.; Zhu, J. The Chemistry of Organic Silicon Compounds.; Wiley: New York, 1998; p 1687.
3. Luh, T.; Liu., S. The Chemistry of Organic Silicon Compounds; Wiley: New York, 1998; Vol. 2, p 1793.
4. Harrod, J. F.; Chalk, A. J.; Davies, N. R. Nature 1965, 205, 280.
5. Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1965, 87, 16.
6. (a) Harrod, J. F., Chalk, A. J., Wender, I., Pino, P., Eds. In Organic Synthesis via Metal Carbonyls; Wiley: New York, 1977; Vol. 2, p 673.
7. (b) Schroeder, M. A.; Wrighton, M. S. J. Organomet. Chem. 1977, 128, 345.
8. Esteruelas, M. A.; Olivan, M.; Oro, L. A.; Tolosa, J. I. J. Organomet. Chem. 1995, 487, 143.
9. Brookhart, M.; Grant, B. E. J. Am. Chem. Soc. 1993, 115, 2151.
10. LaPointe, A. M.; Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 906.
11. Shimizu, R.; Fuchikami, T. Tetrahedron Lett. 2000, 41, 907.
12. Jun, C. H.; Crabtree, R. H. J. Organomet. Chem. 1993, 447, 177.
13. Bergens, S. H.; Noheda, P.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 2128.
14. Maruyama, Y.; Yamamura, K.; Sagawa, T.; Katayama, H.; Ozawa, F. Organometallics 2000, 19, 1308.
15. Adams, R. D.; Barnard, T. S. Organometallics 1998, 17, 2567.
16. Maruyama, Y.; Yamamura, K.; Nakayama, I.; Yoshiuchi, K.; Ozawa, F. J. Am. Chem. Soc. 1998, 120, 1421.
17. Esteruelas, M. A.; Herrero, J.; Oro, L. A. Organometallics 1993, 12, 2377.
18. Itami, K.; Mitsudo, K.; Nishino, A.; Yoshida, J. J. Org. Chem. 2002, 67, 2645.
19. Cervantes, J.; Gonzalez-AlaTorre, G.; Rohack, D.; Pannell, K. H. Appl. Organomet. Chem. 2000, 14, 146.
20. Chung, L. W.; Wu, Y. D.; Trost, B. M.; Ball, Z. T. J. Am. Chem. Soc. 2003, 125, 11578.
21. Crabtree, R. H. New J. Chem. 2003, 27, 771.
22. Marciniec, B. Coord. Chem. Rev. 2005, 249, 2374.
23. Lachaize, S.; Sabo-Etienne, S.; Donnadieu, B.; Chaudret, B. Chem. Commun. 2003, 214.
24. Faller, J. W.; D'Alliessi, D. G. Organometallics 2002, 21, 1743.
25. Furmeier, S.; Griep-Raming, J.; Hayen, A.; Metzger, J. O. Chem.-Eur. J. 2005, 11, 5545.
26. Furmeier, S.; Metzger, J. O. J. Am. Chem. Soc. 2004, 126, 14485.
27. Santos, L. S.; Pavam, C. H.; Almeida, W. P.; Coelho, F.; Eberlin, M. N. Angew. Chem., Int. Ed. 2004, 43, 4330.
28. Sabino, A. A.; Machado, A. H. L.; Correia, C. R. D.; Eberlin, M. N. Angew. Chem., Int. Ed. 2004, 43, 2514.
29. Chen, H.; Zheng, X. B.; Yang, P. X.; Cooks, R. G. Chem. Commun. 2004, 688.
30. Meyer, S.; Koch, R.; Metzger, J. O. Angew. Chem., Int. Ed. 2003, 42, 4700.
31. Zhang, X. Y.; Chen, P. Chem.-Eur. J. 2003, 9, 1852.
32. Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J. O. Angew. Chem., Int. Ed. 2002, 41, 2738.
33. DePuy, C. H. J. Org. Chem. 2002, 67, 2393.
34. Aliprantis, A. O.; Canary, J. W. J. Am. Chem. Soc. 1994, 116, 6985.
35. Hwang, L. K.; Na, Y.; Lee, J.; Do, Y.; Chang, S. Angew. Chem., Int. Ed. 2005, 44, 6166.
36. Guo, H.; Qian, R.; Liao, Y. X.; Ma, S. M.; Quo, Y. L. J. Am. Chem. Soc. 2005, 127, 13060.
37. Qian, R.; Guo, H.; Liao, Y. X.; Guo, Y. L.; Ma, S. M. Angew. Chem., Int. Ed. 2005, 44, 4771.
38. Santos, L. S.; Metzger, J. O. Angew. Chem., Int. Ed. 2006, 45, 977.
39. Peris, E.; Crabtree, R. H. C. R. Chimie 2003, 6, 33.
40. Peris, E.; Crabtree, R. H. Coord. Chem. Rev. 2004, 245, 2239.
41. Mas-Marza, E.; Poyatos, M.; Sanau, M.; Peris, E. Inorg. Chem. 2004, 43, 2213.
42. Poyatos, M.; Mas-Marza, E.; Mata, J. A.; Sanau, M.; Peris, E. Eur. J. Inorg. Chem. 2003, 1215.
43. Mas-Marza, E.; Sanau, M.; Peris, E. Inorg. Chem. 2005, 44, 9961.
44. Wang, H. M. J.; Lin, I. J. B. Organometallics 1998, 17, 972.
45. Garrison, J. C.; Youngs, W. J. Chem. Rev. 2005, 105, 3978
46. Lin, I. J. B.; Vasam, C. S. Comments Inorg. Chem. 2004, 25, 75.
47. Viciano, M.; Poyatos, M.; Sanau, M.; Peris, E.; Rossin, A.; Ujaque, G.; Lledos, A. Organometallics 2006, 25, 1120.
48. Mas-Marza, E.; Peris, E.; Castro-Rodriguez, I.; Meyer, K. Organometallics 2005, 24, 3158.
49. Viciano, M.; Mas-Marza, E.; Poyatos, M.; Sanau, M.; Crabtree, R. H.; Peris, E. Angew. Chem., Int. Ed. 2005, 44, 444.
50. Miecznikowski, J. R.; Crabtree, R. H. Organometallics 2004, 23, 629.
51. Chianese, A. R.; Kovacevic, A.; Zeglis, B. M.; Faller, J. W.; Crabtree, R. H. Organometallics 2004, 23, 2461.
52. Huang, J. K.; Schanz, H. J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 2370.
53. Goikhman, R.; Milstein, D. Chem.-Eur. J. 2005, 11, 2983.
54. Bosnich, B. Acc. Chem. Res. 1998, 31, 667.
55. Ojima, I.; Clos, N.; Donovan, R. J.; Ingallina, P. Organometallics 1990, 9, 3127.
56. Tanke, R. S.; Crabtree, R. H. J. Am. Chem. Soc. 1990, 112, 7984.
57. Tanke, R. S.; Crabtree, R. H. J. Chem. Soc., Chem. Commun. 1990, 1056.
58. Hinderling, C.; Plattner, D. A.; Chen, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 243.
59. Itoh, M.; Kobayashi, M.; Ishikawa, J. Organometallics 1997, 16, 3068.
60. Ishikawa, J.; Inoue, K.; Itoh, M. J. Organomet. Chem. 1998, 552, 303.
61. Corberan, R.; Sanau, M.; Peris, E. J. Am. Chem. Soc. 2006, 128, 3974.
62. Lin, Y.; Nomiya, K.; Finke, R. G. Inorg. Chem. 1993, 32, 6040.
63. SAINT, Bruker Analytical X-ray System, version 5.0; Bruker AXS: Madison, WI, 1998.
64. Sheldrick, G. M. SHELXTL, version 6.1; Bruker AXS, Inc.: Madison, WI, 2000.