Density functional study on the mechanism of palladium(0)-catalyzed thioboration reaction of alkynes. Differences between Pd(0) and Pt(0) catalysts and between thioboration and diboration

Organometallics

Volumn 17, Issue 7, 1998, Pages 1383-1392

  Cui, Qiang ^a   Musaev, Djamaladdin G ^a   Morokuma, Keiji ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001206279     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970834z     Document Type: Article

References (30)

1. (a) Brown, H. C. Boranes in Organic Chemistry; Cornell University Press: London, 1972.
2. (b) Brown, H. C. Organic Synthesis via Organoboranes; Wiley-Interscience: New York, 1975.
3. (c) Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic Press: New York, 1988.
4. For example, see: (a) Lesley, G.; Nguyen, P.; Taylor, N. J.; Marder, T. B.; Scott, A. J.; Clegg, W.; Norman, N. C. Organometallics 1996, 15, 5137 and references therein. (b) Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018. (c) Iverson, C. N.; Smith, M. R. A., III J. Am. Chem. Soc. 1995, 117, 4403. (d) Suzuki, A. Pure Appl. Chem. 1994, 66, 213. (e) Gridnev, I. D.; Miyaura, N.; Suzuki, A. Organometallics 1993, 12, 589. (g) Iverson, C. N.; Smith, M. R., III Organometallics 1996, 15, 5155.
5. For example, see: (a) Lesley, G.; Nguyen, P.; Taylor, N. J.; Marder, T. B.; Scott, A. J.; Clegg, W.; Norman, N. C. Organometallics 1996, 15, 5137 and references therein. (b) Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018. (c) Iverson, C. N.; Smith, M. R. A., III J. Am. Chem. Soc. 1995, 117, 4403. (d) Suzuki, A. Pure Appl. Chem. 1994, 66, 213. (e) Gridnev, I. D.; Miyaura, N.; Suzuki, A. Organometallics 1993, 12, 589. (g) Iverson, C. N.; Smith, M. R., III Organometallics 1996, 15, 5155.
6. For example, see: (a) Lesley, G.; Nguyen, P.; Taylor, N. J.; Marder, T. B.; Scott, A. J.; Clegg, W.; Norman, N. C. Organometallics 1996, 15, 5137 and references therein. (b) Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018. (c) Iverson, C. N.; Smith, M. R. A., III J. Am. Chem. Soc. 1995, 117, 4403. (d) Suzuki, A. Pure Appl. Chem. 1994, 66, 213. (e) Gridnev, I. D.; Miyaura, N.; Suzuki, A. Organometallics 1993, 12, 589. (g) Iverson, C. N.; Smith, M. R., III Organometallics 1996, 15, 5155.
7. For example, see: (a) Lesley, G.; Nguyen, P.; Taylor, N. J.; Marder, T. B.; Scott, A. J.; Clegg, W.; Norman, N. C. Organometallics 1996, 15, 5137 and references therein. (b) Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018. (c) Iverson, C. N.; Smith, M. R. A., III J. Am. Chem. Soc. 1995, 117, 4403. (d) Suzuki, A. Pure Appl. Chem. 1994, 66, 213. (e) Gridnev, I. D.; Miyaura, N.; Suzuki, A. Organometallics 1993, 12, 589. (g) Iverson, C. N.; Smith, M. R., III Organometallics 1996, 15, 5155.
8. For example, see: (a) Lesley, G.; Nguyen, P.; Taylor, N. J.; Marder, T. B.; Scott, A. J.; Clegg, W.; Norman, N. C. Organometallics 1996, 15, 5137 and references therein. (b) Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018. (c) Iverson, C. N.; Smith, M. R. A., III J. Am. Chem. Soc. 1995, 117, 4403. (d) Suzuki, A. Pure Appl. Chem. 1994, 66, 213. (e) Gridnev, I. D.; Miyaura, N.; Suzuki, A. Organometallics 1993, 12, 589. (g) Iverson, C. N.; Smith, M. R., III Organometallics 1996, 15, 5155.
9. For example, see: (a) Lesley, G.; Nguyen, P.; Taylor, N. J.; Marder, T. B.; Scott, A. J.; Clegg, W.; Norman, N. C. Organometallics 1996, 15, 5137 and references therein. (b) Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018. (c) Iverson, C. N.; Smith, M. R. A., III J. Am. Chem. Soc. 1995, 117, 4403. (d) Suzuki, A. Pure Appl. Chem. 1994, 66, 213. (e) Gridnev, I. D.; Miyaura, N.; Suzuki, A. Organometallics 1993, 12, 589. (g) Iverson, C. N.; Smith, M. R., III Organometallics 1996, 15, 5155.
10. (a) Musaev, D. G.; Mebel, A. M.; Morokuma, K. J. Am. Chem. Soc. 1994, 116, 10693.
11. (b) Musaev, D. G.; Morokuma, K. J. Phys. Chem. 1996, 100, 6509.
12. (c) Dorigo, A. E.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 878.
13. (d) Cui, Q.; Musaev, D. G.; Morokuma, K. Organometallics 1998, 17, 742.
14. (e) Cui, Q.; Musaev, D. G.; Morokuma, K. Organometallics 1997, 16, 1355.
15. Ishiyama, T.; Nishijima, K.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 7219.
16. (a) Mikhailov, B. M.; Bubnov, Y. N. In Organoboron Compounds in Organic Synthesis; OPA: Amsterdam, 1984; pp 693.
17. (b) Mukaiyama, T.; Inomata, K.; Muraki, M. J. Am. Chem. Soc. 1973, 95, 967.
18. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
19. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
20. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
21. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
22. Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284.
23. Ehlers, A. W.; Böhme, M.; Dapprich, S.; Gobbi, A.; Höllwarth, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; and Frenking, G. Chem. Phys. Lett. 1993, 208, 111.
24. (a) Dunning, T. M., Jr. J. Chem. Phys. 1971, 55, 716.
25. (b) Dunning, T. M., Jr. J. Chem. Phys. 1970, 53, 2823.
26. (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J. B.; Stefanov, B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision D.3; Gaussian, Inc.: Pittsburgh, PA, 1995.
27. (b) Cui, Q.; Musaev, D. G.; Svensson, M.; Morokuma, K. J. Phys. Chem. 1996, 100, 10936.
28. Blomberg, M. R. A.; Siegbahn, P. E. M.; Svensson, M. J. Chem. Phys. 1996, 104, 9546.
29. (a) Low, J. J.; Goddard, W. A., III J. Am. Chem. Soc. 1986, 108, 6115.
30. (b) Low, J. J.; Goddard, W. A., III Organometallics 1986, 5, 609.