Palladium(II) terminal phosphido complexes derived from cyclometalated dimesitylphosphine: Synthesis, structure, and low-barrier phosphorus inversion

Organometallics

Volumn 21, Issue 15, 2002, Pages 3208-3214

  Zhuravel, Michael A ^a   Glueck, David S ^a   Zakharov, Lev N ^b   Rheingold, Arnold L ^b  

^a Dartmouth College   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM COMPOUNDS; PHOSPHORUS; POSITIVE IONS; SYNTHESIS (CHEMICAL);

DEPROTONATION;

ORGANOMETALLICS;

EID: 0000870448     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om020249k     Document Type: Article

References (44)

1. Wicht, D. K.; Glueck, D. S. In Catalytic Heterofunctionalization: From Hydroamination to Hydrozirconation; Togni, A., Crutzmacher, H., Eds.; Wiley-VCH: Weinheim, Germany, 2001; pp 143-170.
2. For selected examples of catalytic phosphination, see: (a) Lucht, B. L.; St. Onge, N. O. Chem. Commun. 2000, 2097-2098.
3. (b) Cai, D.; Payack, J. F.; Bender, D. H.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. Org. Synth. 1999, 76, 6-11.
4. (c) Herd, O.; Hessler, A.; Hingst, M.; Machnitzki, P.; Tepper, M.; Stelzer, O. Catal. Today 1998, 42, 413-420.
5. (d) Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748-753.
6. For Pt terminal phosphido complexes, see: (a) Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950-953.
7. (b) Wicht, D. K.; Kourkine, I. V.; Kovacik, I.; Glueck, D. S.; Concolino, T. E.; Yap, G. P. A.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5381-5394.
8. (c) Wicht, D. K.; Glueck, D. S.; Liable-Sands, L. M.; Rheingold, A. L. Organometallics 1999, 18, 5130-5140.
9. (d) Wicht, D. K.; Kovacik, I.; Glueck, D. S.; Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5141-5151.
10. (e) Kourkine, I. V.; Sargent, M. D.; Glueck, D. S. Organometallics 1998, 17, 125-127.
11. (f) Wicht, D. K.; Paisner, S. N.; Lew, B. M.; Glueck, D. S.; Yap, G. P. A.; Liable-Sands, L. M.; Rheingold, A. L.; Haar, C. M.; Nolan, S. P. Organometallics 1998, 17, 652-660.
12. (g) Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039-5040.
13. (h) Cecconi, F.; Ghilardi, C. A.; Midollini, S.; Moneti, S.; Orlandini, A.; Scapacci, G. Inorg. Chim. Acta 1991, 189, 105-110.
14. (i) Handler, A.; Peringer, P.; Muller, E. P. J. Chem. Soc., Dalton Trans. 1990, 3725-3727.
15. (j) Maassarani, F.; Davidson, M. F.; Wehman-Ooyevaar, I. C. M.; Grove, D. M.; van Koten, M. A.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. Inorg. Chim. Acta 1995, 235, 327-338.
16. (k) Schaefer, H.; Binder, D. Z. Anorg. Allg. Chem. 1988, 560, 65-79.
17. (l) Allen, C. W.; Ebsworth, E. A. V.; Henderson, S. G.; Rankin, D. W. H.; Robertson, H. E.; Turner, B.; Whitelock, J. D. J. Chem. Soc., Dalton Trans. 1986, 1333-1338.
18. For Ni terminal phosphido complexes, see: (a) Schaefer, H.; Binder, D.; Deppisch, B.; Mattern, G. Z. Anorg. Allg. Chem. 1987, 546, 79-98.
19. (b) Schaefer, H. Z. Anorg. Allg. Chem. 1979, 459, 157-169.
20. (c) Driess, M.; Pritzkow, H.; Winkler, U. J. Organomet. Chem. 1997, 529, 313-321.
21. (d) Melenkivitz, R.; Mindiola, D. J.; Hillhouse, G. L. J. Am. Chem. Soc. 2002, 124, 3846-3847.
22. For Pd bridging phosphido complexes, see: (a) Leoni, P.; Marchetti, P.; Papucci, S.; Pasquali, M. J. Organomet. Chem. 2000, 593-594, 12-18.
23. (b) Zhuravel, M. A.; Moncarz, J. R.; Glueck, D. S.; Lam, K.-C.; Rheingold, A. L. Organometallics 2000, 19, 3447-3454.
24. (c) Review: Mealli, C.; Ienco, A.; Galindo, A.; Carreño, E. P. Inorg. Chem. 1999, 38, 4620-4625.
25. (d) See also: Belykh, L. B.; Cherenkova, T. V.; Shmidt, F. K. Russ. J. Coord. Chem. (Engl. Transl.) 1999, 25, 418-422.
26. 2), see: David, M.-A.; Wicht, D. K.; Glueck, D. S.; Yap, G. P. A.; Liable-Sands, L. M.; Rheingold, A. L. Organometallics 1997, 16, 4768-4770.
27. (a) Zhuravel, M. A. Ph.D. Thesis, Dartmouth College, 2000.
28. (b) Zhuravel, M. A.; Wicht, D. K.; Sweeder, R. D.; Moncarz, J. R.; Glueck, D. S.; Lam, K.-C.; Yap, G. P. A., Incarvito, C. D.; Sommer, R.; Rheingold, A. L. Manuscript in preparation.
29. Zhuravel, M. A.; Grewal, N. S.; Glueck, D. S.; Lam, K.-C.; Rheingold, A. L. Organometallics 2000, 19, 2882-2890.
30. Deeming, A. J.; Doherty, S.; Marshall, J. E,; Powell, J. L.; Senior, A. M. J. Chem. Soc., Dalton Trans. 1993, 1093-1100.
31. Friebolin, H. In Basic One- and Two-Dimensional NMR Spectroscopy, 2nd ed.; VCH: New York, 1993; pp 287-314.
32. (a) Rogers, J. R.; Wagner, T. P. S.; Marynick, D. S. Inorg. Chem. 1994, 33, 3104-3110.
33. (b) Buhro, W. E.; Gladysz, J. A. Inorg. Chem. 1985, 24, 3505-3507.
34. (c) Simpson, R. D.; Bergman, R. G. Organometallics 1992, 11, 3980-3993.
35. (d) Crisp, G. T.; Salem, G.; Wild, S. B.; Stephan, F. S. Organometallics 1989, 8, 2360-2367.
36. (e) Malisch, W.; Maisch, R.; Meyer, A.; Greissinger, D.; Gross, E.; Colquhoun, E. J.; McFarlane, W. Phosphorus Sulfur Relat. Elem. 1983, 18, 299-302.
37. (f) Baker, R. T.; Whitney, J. G.; Wreford, S. S. Organometallics 1983, 2, 1049-1051.
38. (g) Bonnet, G.; Kubicki, M. M.; Moise, C.; Lazzaroni, R.; Salvadori, P.; Vitulli, G. Organometallics 1992, 11, 964-967.
39. (h) Fryzuk, M. D.; Joshi, K.; Chadha, R. K.; Rettig, S. J. J. Am. Chem. Soc. 1991, 113, 8724-8736.
40. (i) References 3a-d.
41. 2 protons as well as the o-Me groups and m-H protons would be inequivalent. In this case, the measured barriers would reflect only P-C(Mes) rotation. We favor the simpler explanation in the text, however.
42. Dekker, G. P. C. M.; Buijs, A.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Smeets, W. J. J.; Spek, A. L.; Wang, Y. F.; Stam, C. H. Organometallics 1992, 11, 1937-1948.
43. Clark, H. C.; Manzer, L. E. Inorg. Chem. 1974, 13, 1291-1297.
44. Bartlett, R. A.; Olmstead, M. M.; Power, P. P.; Sigel, G. A. Inorg. Chem. 1987, 26, 1941-1946.