Reaction mechanism of palladium-catalyzed silastannation of allenes by density functional theory

Journal of Computational Chemistry

Volumn 30, Issue 9, 2009, Pages 1521-1531

  Wang, Meiyan ^a,b   Cheng, Lin ^a,b   Hong, Bo ^a,c   Wu, Zhijian ^a  

^a CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c JILIN AGRICULTURAL UNIVERSITY   (China)

Author keywords

Density functional method; Palladium catalyzed addition; Reaction mechanism; Silylstannanes to allenes

Indexed keywords

ALLENES; BACK-DONATION; DENSITY FUNCTIONAL METHOD; DENSITY-FUNCTIONAL METHODS; ELECTRON DONATION; ELECTRONIC MECHANISMS; INSERTION PRODUCTS; OVERALL REACTIONS; REACTION MECHANISM; SILYLSTANNANES TO ALLENES;

DENSITY FUNCTIONAL THEORY; SILANES; SILICON; TIN;

PALLADIUM;

ALKADIENE; ORGANOMETALLIC COMPOUND; PALLADIUM; SILICON; TIN;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMISTRY; COMPUTER SIMULATION; SYNTHESIS;

ALKADIENES; CATALYSIS; COMPUTER SIMULATION; MODELS, CHEMICAL; ORGANOMETALLIC COMPOUNDS; PALLADIUM; SILICON; TIN;

EID: 67650128413     PISSN: 01928651     EISSN: 1096987X     Source Type: Journal    
DOI: 10.1002/jcc.21176     Document Type: Article

References (43)

1. Beletskaya, I.; Moberg, C. Chem Rev 1999, 99, 3435.
2. Beletskaya, I.; Moberg, C. Chem Rev 2006, 106, 2320.
3. Suginome, M.; Ito, Y. Chem Rev 2000, 100, 3221.
4. Clarke, M. L. Polyhedron 2001, 20, 151.
5. Ramírez, J.; Lillo, V.; Segarra, A. M.; Fernández, E. C R Chimie 2007, 10, 138.
6. Marder, T. B.; Norman, N. C. Top Catal 1998, 5, 63.
7. Ishiyama, T.; Miyaura, N. Chem Rec 2004, 3, 271.
8. Ishiyama, T.; Miyaura, N. J Organomet Chem 2000, 611, 392.
9. Suginome, M.; Ito, Y. J Organomet Chem 2003, 680, 43.
10. Burks, H. E.; Morken, J. P. Chem Commun 2007, 4717.
11. Suginome, M.; Ohmori, Y.; Ito, Y. J Organomet Chem 2000, 611, 403.
12. Horn, K. A. Chem Rev 1995, 95, 1317.
13. Mitchell, T. N.; Killing, H.; Dicke, R.; Wickenkamp, R. J Chem Soc Chem Commun 1985, 354.
14. Mitchell, T. N.; Schneider, U. J Organomet Chem 1991, 407, 319.
15. Koerber, K.; Gore, J.; Vatele, J.-M. Tetrahedron Lett 1991, 32, 1187.
16. Barrett, A. G. M.; Wan, P. W. H. J Org Chem 1996, 61, 8667.
17. Jeganmohan, M.; Shanmugasundaram, M.; Chang, K.-J.; Cheng, C.-H. Chem Commun 2002, 2552.
18. Shin, S.; RajanBabu, T. V. J Am Chem Soc 2001, 123, 8416.
19. Kang, S.-K.; Ha, Y.-H.; Ko, B.-S.; Lim, Y.; Jung, J. Angew Chem Int Ed 2002, 41, 343.
20. Kumareswaran, R.; Gallucci, J.; RajanBabu, T. V. J Org Chem 2004, 69, 9151.
21. Kang, S.-K.; Baik, T.-G.; Kulak, A. N.; Ha, Y.-H.; Lim, Y.; Park, J. J Am Chem Soc 2000, 122, 11529.
22. Wesquet, A. O.; Kazmaier, U. Angew Chem Int Ed 2008, 47, 3050.
23. Abe, Y.; Kuramoto, K.; Ehara, M.; Nakatsuji, H.; Suginome, M.; Murakami, M.; Ito, Y. Organometallics 2008, 27, 1736.
24. Hada, M.; Tanaka, Y.; Ito, M.; Murakami, M.; Amii, H.; Ito, Y.; Nakatsuji, H. J Am Chem Soc 1994, 116, 8754.
25. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, J.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Gaussian, Pittsburgh, PA, 2003.
26. Becke, A. D. Phys Rev A 1988, 38, 3098.
27. Lee, C.; Yang, W.; Parr, R. G. Phys Rev B 1988, 37, 785.
28. Becke, A. D. J Chem Phys 1993, 98, 5648.
29. Hay, P. J.; Wadt, W. R. J Chem Phys 1985, 82, 299.
30. Ehlers, A. W.; Böhme, M.; Dapprich, S.; Gobbi, A.; Höllwarth, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem Phys Lett 1993, 208, 111.
31. Huzinaga, S., Ed. Gaussian Basis Sets for Molecular Calculations; Elsevier: Amsterdam, 1984.
32. Fukui, K. J Phys Chem 1970, 74, 4161.
33. Fukui, K. Acc Chem Res 1981, 14, 363.
34. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO Version 3.1.
35. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem Rev 1988, 88, 899.
36. Foster, J. P.; Weinhold, F. J Am Chem Soc 1980, 102, 7211.
37. Sakaki, S.; Kai, S.; Sugimoto, M. Organometallics 1999, 18, 4825.
38. Zhu, J.; Lin, Z. Y.; Marder, T. B. Inorg Chem 2005, 44, 9384.
39. Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. J Am Chem Soc 1994, 116, 7258.
40. Zhao, H. T.; Lin, Z. Y.; Marder, T. B. J Am Chem Soc 2006, 128, 15637.
41. Dang, L.; Zhao, H. T.; Lin, Z. Y.; Marder, T. B. Organometallics 2007, 26, 2824.
42. Cui, Q.; Musaev, D. G.; Morokuma, K. Organometallics 1997, 16, 1355.
43. Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 1999, 18, 4015.