Lewis acids accelerate reductive elimination of RCN from P2Pd(R)(CN)

Organometallics

Volumn 18, Issue 3, 1999, Pages 297-299

  Huang, Jinkun ^a   Haar, Christopher M ^a   Nolan, Steven P ^a   Marcone, John E ^b   Moloy, Kenneth G ^b  

^a UNIVERSITY OF NEW ORLEANS   (United States)

^b DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001030517     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980897x     Document Type: Article

References (33)

1. (a) Goldberg, K. I.; Yan, J.; Breitung, E. M. J. Am. Chem. Soc. 1995, 117, 6889, and references therein.
2. (b) Brown, J. M.; Cooley, N. A. Chem. Rev. 1988, 88, 1031, and references therein.
3. (c) Byers, P. K.; Canty, A. J.; Crespo, M.; Puddephatt, R. J.; Scott, J. D. Organometallics 1988, 7, 1363, and references therein.
4. (d) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933.
5. Atwood, J. D. Inorganic and Organometallic Reaction Mechanisms; Brooks/Cole: Monterey, CA, 1985; p 177.
6. Marcone, J. E.; Moloy, K. G. J. Am. Chem. Soc. 1998, 120, 8527.
7. A detailed study of the factors influencing C-S bond-forming reductive elimination has recently appeared: Mann, G.; Baranano, D.; Hartwig, J. F.; Rheingold, A. L.; Guzei, I. A. J. Am. Chem. Soc. 1998, 120, 9205.
8. 2; DIOP = 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane.
9. (a) Calhorda, M. J.; Brown, J. M.; Cooley, N. A. Organometallics 1991, 10, 1431.
10. (b) Cleary, B. P.; Mehta, R.; Eisenberg, R. Organometallics 1995, 14, 2297, and references therein.
11. (c) Hill, G. S.; Puddephatt, R. J. Organometallics 1998, 17, 1478.
12. Horwitz, C. P.; Shriver, D. F. Adv. Organomet. Chem. 1984, 23, 219.
13. (a) Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry, 5th ed.; Wiley: New York, 1988; pp 253-255.
14. (b) Woodcock, C.; Shriver, D. F. Inorg. Chem. 1986, 25, 2137, and references therein.
15. a) Tolman, C. A.; McKinney, R. J.; Seidel, W. C.; Druliner, J. D.; Stevens, W. R. Adv. Catal. 1985, 33, 1.
16. (b) McKinney, R. J.; Nugent, W. A. Organometallics 1989, 8, 2871.
17. See Supporting Information for complete details.
18. CN as the Lewis acidity is increased is likely attributable to the accompanying increase in metal-to-ligand back-bonding. (a) Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, 4th ed.; Wiley-Interscience: New York, 1986; p 272. b) Drago, R. S. Physical Methods in Chemistry; W. B. Saunders: Philadelphia, 1977; p 177. (c) Kristoff, J. S.; Shriver, D. F. Inorg. Chem. 1973, 12, 1788. (d) Shriver, D. F.; Swanson, B. Inorg. Chem. 1971, 10, 1354. (e) Purcell, K. F.; Drago, R. S. J. Am. Chem. Soc. 1966, 88, 919.
19. CN as the Lewis acidity is increased is likely attributable to the accompanying increase in metal-to-ligand back-bonding. (a) Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, 4th ed.; Wiley-Interscience: New York, 1986; p 272. b) Drago, R. S. Physical Methods in Chemistry; W. B. Saunders: Philadelphia, 1977; p 177. (c) Kristoff, J. S.; Shriver, D. F. Inorg. Chem. 1973, 12, 1788. (d) Shriver, D. F.; Swanson, B. Inorg. Chem. 1971, 10, 1354. (e) Purcell, K. F.; Drago, R. S. J. Am. Chem. Soc. 1966, 88, 919.
20. CN as the Lewis acidity is increased is likely attributable to the accompanying increase in metal-to-ligand back-bonding. (a) Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, 4th ed.; Wiley-Interscience: New York, 1986; p 272. b) Drago, R. S. Physical Methods in Chemistry; W. B. Saunders: Philadelphia, 1977; p 177. (c) Kristoff, J. S.; Shriver, D. F. Inorg. Chem. 1973, 12, 1788. (d) Shriver, D. F.; Swanson, B. Inorg. Chem. 1971, 10, 1354. (e) Purcell, K. F.; Drago, R. S. J. Am. Chem. Soc. 1966, 88, 919.
21. CN as the Lewis acidity is increased is likely attributable to the accompanying increase in metal-to-ligand back-bonding. (a) Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, 4th ed.; Wiley-Interscience: New York, 1986; p 272. b) Drago, R. S. Physical Methods in Chemistry; W. B. Saunders: Philadelphia, 1977; p 177. (c) Kristoff, J. S.; Shriver, D. F. Inorg. Chem. 1973, 12, 1788. (d) Shriver, D. F.; Swanson, B. Inorg. Chem. 1971, 10, 1354. (e) Purcell, K. F.; Drago, R. S. J. Am. Chem. Soc. 1966, 88, 919.
22. CN as the Lewis acidity is increased is likely attributable to the accompanying increase in metal-to-ligand back-bonding. (a) Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, 4th ed.; Wiley-Interscience: New York, 1986; p 272. b) Drago, R. S. Physical Methods in Chemistry; W. B. Saunders: Philadelphia, 1977; p 177. (c) Kristoff, J. S.; Shriver, D. F. Inorg. Chem. 1973, 12, 1788. (d) Shriver, D. F.; Swanson, B. Inorg. Chem. 1971, 10, 1354. (e) Purcell, K. F.; Drago, R. S. J. Am. Chem. Soc. 1966, 88, 919.
23. (a) Nolan, S. P.; Hoff, C. D.; Landrum, J. T. J. Organomet. Chem. 1985, 282, 357.
24. (b) Nolan, S. P.; Lopez de la Vega, R.; Hoff C. D. Inorg. Chem. 1986, 25, 4446.
25. 3: (c) Eisch, J. J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, A., Eds.; Pergamon Press: Oxford, U.K., 1982; Vol. 1, Chapter 6, p 593.
26. 3: (c) Eisch, J. J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, A., Eds.; Pergamon Press: Oxford, U.K., 1982; Vol. 1, Chapter 6, p 593.
27. 3: (c) Eisch, J. J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, A., Eds.; Pergamon Press: Oxford, U.K., 1982; Vol. 1, Chapter 6, p 593.
28. Shriver, D. F. J. Am. Chem. Soc. 1963, 85, 1405.
29. (a) Kranenburg, M.; Delis, J. G. P.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Vrieze, K.; Veldman, N.; Spek, A. L.; Goubitz, K.; Fraanje, J. J. Chem. Soc., Dalton Trans. 1997, 1839.
30. (b) Portnoy, M.; Ben-David, Y.; Rousso, I.; Milstein, D. Organometallics 1994, 13, 3465.
31. -: Weller, F.; Dehnicke, K. J. Organomet. Chem. 1972, 36, 23.
32. -: Weller, F.; Dehnicke, K. J. Organomet. Chem. 1972, 36, 23.
33. This conclusion assumes the effects are additive.