Oxidative addition of dimesitylphosphine to platinum(0): P-H vs P-C activation

Organometallics

Volumn 17, Issue 2, 1998, Pages 125-127

  Kourkine, Igor V ^a   Sargent, Matthew D ^a   Glueck, David S ^a  

^a Dartmouth College   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 3743120482     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970754v     Document Type: Article

References (31)

1. (a) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis: the Applications and Chemistry of Catalysis by Soluble Transition Metal Complexes, 2nd ed.; Wiley: New York, 1992.
2. (b) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
3. See Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039-5040 and ref 1 therein for examples.
4. Garrou, P. E. Chem. Rev. 1985, 85, 171-185.
5. For related observations, see: (a) C-H vs C-Si addition Hofmann, P.; Heiss, H.; Neiteler, P.; Muller, G.; Lachmann, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 880-882. Hofmann, P. In Organosilicon Chemistry: From Molecules to Materials; Auner, N., Weis, J., Eds.; VCH: Weinheim, Germany, 1994; pp 231-250. (b) N-H vs N-C addition Bonanno, J. B.; Henry, T. P.; Neithamer, D. R.; Wolczanski, P. T.; Lobkovsky, E. B. J. Am. Chem. Soc. 1996, 118, 5132-5133. (c) C-H vs C-C addition Rybtchinski, B.; Vigalok, A.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 1996, 118, 12406-12415.
6. For related observations, see: (a) C-H vs C-Si addition Hofmann, P.; Heiss, H.; Neiteler, P.; Muller, G.; Lachmann, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 880-882. Hofmann, P. In Organosilicon Chemistry: From Molecules to Materials; Auner, N., Weis, J., Eds.; VCH: Weinheim, Germany, 1994; pp 231-250. (b) N-H vs N-C addition Bonanno, J. B.; Henry, T. P.; Neithamer, D. R.; Wolczanski, P. T.; Lobkovsky, E. B. J. Am. Chem. Soc. 1996, 118, 5132-5133. (c) C-H vs C-C addition Rybtchinski, B.; Vigalok, A.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 1996, 118, 12406-12415.
7. For related observations, see: (a) C-H vs C-Si addition Hofmann, P.; Heiss, H.; Neiteler, P.; Muller, G.; Lachmann, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 880-882. Hofmann, P. In Organosilicon Chemistry: From Molecules to Materials; Auner, N., Weis, J., Eds.; VCH: Weinheim, Germany, 1994; pp 231-250. (b) N-H vs N-C addition Bonanno, J. B.; Henry, T. P.; Neithamer, D. R.; Wolczanski, P. T.; Lobkovsky, E. B. J. Am. Chem. Soc. 1996, 118, 5132-5133. (c) C-H vs C-C addition Rybtchinski, B.; Vigalok, A.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 1996, 118, 12406-12415.
8. For related observations, see: (a) C-H vs C-Si addition Hofmann, P.; Heiss, H.; Neiteler, P.; Muller, G.; Lachmann, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 880-882. Hofmann, P. In Organosilicon Chemistry: From Molecules to Materials; Auner, N., Weis, J., Eds.; VCH: Weinheim, Germany, 1994; pp 231-250. (b) N-H vs N-C addition Bonanno, J. B.; Henry, T. P.; Neithamer, D. R.; Wolczanski, P. T.; Lobkovsky, E. B. J. Am. Chem. Soc. 1996, 118, 5132-5133. (c) C-H vs C-C addition Rybtchinski, B.; Vigalok, A.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 1996, 118, 12406-12415.
9. 2 per 1 equiv of 1 are complete in ∼250 h, with similar yields.
10. 31P NMR in comparison to an authentic sample, see: Clark, H. C.; Kapoor, P. N.; McMahon, I. J. J. Organomet. Chem. 1984, 265, 107-115.
11. COD = 1,5-cyclooctadiene. Fallis, K. A.; Anderson, G. K.; Rath, N. P. Organometallics 1993, 12, 2435-2439.
12. For experimental details and characterization data, see the Supporting Information.
13. Pt-P = 3356)). See: Bryndza, H. E.; Calabrese, J. C.; Marsi, M.; Roe, D. C.; Tam, W.; Bercaw, J. E. J. Am. Chem. Soc. 1986, 108, 4805-4813.
14. 3Pt: C, 61.18; H, 5.48. Found: C, 60.95; H, 5.34.
15. 11)(PHMes) were observed.
16. 8
17. 8
18. 8
19. 4) and competitive C-H and C-Si oxidative addition and disproportionation steps.
20. For examples of reversible P-H activation, see: (a) Baker, K. T.; Calabrese, J. C.; Glassman, T. E. Organometallics 1988, 7, 1889-1891. (b) Baker, R. T.; Calabrese, J. C.; Harlow, R. L.; Williams, I. D. Organometallics 1993, 12, 830-841. See also: Schunn, R. A. Inorg. Chem. 1973, 12, 1573-1579.
21. For examples of reversible P-H activation, see: (a) Baker, K. T.; Calabrese, J. C.; Glassman, T. E. Organometallics 1988, 7, 1889-1891. (b) Baker, R. T.; Calabrese, J. C.; Harlow, R. L.; Williams, I. D. Organometallics 1993, 12, 830-841. See also: Schunn, R. A. Inorg. Chem. 1973, 12, 1573-1579.
22. For examples of reversible P-H activation, see: (a) Baker, K. T.; Calabrese, J. C.; Glassman, T. E. Organometallics 1988, 7, 1889-1891. (b) Baker, R. T.; Calabrese, J. C.; Harlow, R. L.; Williams, I. D. Organometallics 1993, 12, 830-841. See also: Schunn, R. A. Inorg. Chem. 1973, 12, 1573-1579.
23. Carmichael, D.; Hitchcock, P. B.; Nixon, J. F.; Pidcock, A. J. Chem. Soc., Chem. Commun. 1988, 1554-1556. This paper states that 7 is a good source of the Pt(dppe) fragment in reactions with Lewis bases, without further details.
24. As pointed out by a referee, the definition of the bond strengths incorporates any changes in the properties of the ancillary ligand bonds during this transformation. For further discussion of this point, see: Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1991, 10, 1875-1887. For similar thermodynamic analyses of proton transfers in the Pt(dppe)(Me)(X) system, see: (a) Bryndza, H. E.; Fong, L. K.; Paciello, R. A.; Tam, W.; Bercaw, J. E. J. Am. Chem. Soc. 1987, 109, 1444-1456. (b) Bryndza, H. E.; Domaille, P. J.; Tam, W.; Fong, L. K.; Paciello, R. A.; Bercaw, J. E. Polyhedron 1988, 7, 1441-1452.
25. As pointed out by a referee, the definition of the bond strengths incorporates any changes in the properties of the ancillary ligand bonds during this transformation. For further discussion of this point, see: Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1991, 10, 1875-1887. For similar thermodynamic analyses of proton transfers in the Pt(dppe)(Me)(X) system, see: (a) Bryndza, H. E.; Fong, L. K.; Paciello, R. A.; Tam, W.; Bercaw, J. E. J. Am. Chem. Soc. 1987, 109, 1444-1456. (b) Bryndza, H. E.; Domaille, P. J.; Tam, W.; Fong, L. K.; Paciello, R. A.; Bercaw, J. E. Polyhedron 1988, 7, 1441-1452.
26. As pointed out by a referee, the definition of the bond strengths incorporates any changes in the properties of the ancillary ligand bonds during this transformation. For further discussion of this point, see: Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1991, 10, 1875-1887. For similar thermodynamic analyses of proton transfers in the Pt(dppe)(Me)(X) system, see: (a) Bryndza, H. E.; Fong, L. K.; Paciello, R. A.; Tam, W.; Bercaw, J. E. J. Am. Chem. Soc. 1987, 109, 1444-1456. (b) Bryndza, H. E.; Domaille, P. J.; Tam, W.; Fong, L. K.; Paciello, R. A.; Bercaw, J. E. Polyhedron 1988, 7, 1441-1452.
27. Martinho Simoes, J. A.; Beauchamp, J. L. Chem. Rev. 1990, 90, 629-688. Because dppe has a greater trans influence than Cl, the Pt-H bond strength in 2 is likely to be lower than this estimated value.
28. Pilcher, G. In The Chemistry of Organophosphorus Compounds; F. R. Hartley, Ed.; John Wiley and Sons: New York, 1990; Vol. 1, pp 127-136.
29. McKean, D. C.; Torto, I.; Morrisson, A. R. J. Phys. Chem. 1982, 86, 307-309.
30. 2 and the model compounds; this reflects the limited data available in organophosphorus thermochemistry (see ref 18). Because of the relatively crude nature of these approximations, the main value of this analysis is its prediction about relative Pt-P bond strengths.
31. Related studies designed to provide an ordering of relative Pt-phosphido bond strengths and to probe the importance of steric and electronic effects are in progress (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. Submitted for publication).