A sterically demanding enolate ligand: Tantalum ligation and pyridine coupling

Organometallics

Volumn 23, Issue 3, 2004, Pages 498-503

  Soo, Han Sen ^a   Diaconescu, Paula L ^a   Cummins, Christopher C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; COMPLEXATION; MONOMERS; POTASSIUM COMPOUNDS; REACTION KINETICS; TANTALUM COMPOUNDS; TRANSITION METALS;

ENOLATE LIGAND; HYDROCARBYL LIGANDS; KETIMIDE LIGANDS; PYRIDINE; SALT METATHESIS REACTION; TANTALUM LIGATION; TRIMETHYLTANTALUM BIS ENOLATE;

ORGANOMETALLICS;

EID: 1142279580     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0303496     Document Type: Article

References (41)

1. LaPointe, R. E.; Wolczanski, P. T.; Mitchell, J. F. J. Am. Chem. Soc. 1986, 108, 6382-6384.
2. Neithamer, D. R.; LaPointe, R. E.; Wheeler, R. A.; Richeson, D. S.; van Duyne, G. D.; Wolczanski, P. T. J. Am. Chem. Soc. 1989, 111, 9056-9072.
3. Gray, S. D.; Smith, D. P.; Bruck, M. A.; Wigley, D. E. J. Am. Chem. Soc. 1992, 114, 5462-5463.
4. Gray, S. D.; Weller, K. J.; Bruck, M. A.; Briggs, P. M.; Wigley, D. E. J. Am. Chem. Soc. 1995, 117, 10678-10693.
5. Strickler, J. R.; Bruck, M. A.; Wigley, D. E. J. Am. Chem. Soc. 1990, 112, 2814-2816.
6. Neithamer, D. R.; Parkanyi, L.; Mitchell, J. F.; Wolczanski, P. T. J. Am. Chem. Soc. 1988, 110, 4421-4423.
7. Weller, K. J.; Filippov, I.; Briggs, P. M.; Wigley, D. E. Organometallics 1998, 17, 322-329.
8. Schaller, C.; Wolczanski, P. T. Inorg. Chem. 1993, 32, 131-144.
9. Lockwood, M. A.; Clark, J. R.; Parkin, B. C.; Rothwell, I. P. Chem. Commun. 1996, 1973-1974.
10. Abbenhuis, H. C. L.; van Belzen, R.; Grove, D. M.; Klomp, A. J. A.; van Mier, G. P. M.; Spek, A. L.; van Koten, G. Organometallics 1993, 12, 210-219.
11. Rietveld, M. H. P.; Elzebe, G. K.; Jastrzebski, J. T. B. H.; Grove, D. M.; Veldman, N.; Spek, A. L.; van Koten, G. Organometallics 1997, 16, 4260-4267.
12. Mullins, S. M.; Bergman, R. G.; Arnold, J. Organometallics 1999, 18, 4465-4467.
13. Vidal, V.; Theolier, A.; Thivolle-Cazat, J.; Basset, J.; Corker, J. J. Am. Chem. Soc. 1996, 118, 4595-4602.
14. Vidal, V.; Theolier, A.; Thivolle-Cazat, J.; Basset, J. J. Chem. Soc., Chem. Commun. 1995, 991-992.
15. Lefort, L.; Coperet, C.; Taoufik, M.; Thivolle-Cazat, J.; Basset, J. Chem. Commun. 2000, 663-664.
16. Jordan, R. F.; Guram, A. S. Organometallics 1990, 9, 2116-2123.
17. Guram, A. S.; Jordan, R. F. Organometallics 1991, 10, 3470-3479.
18. Goe, G. L.; McGill, C. K.; Sherman, A. R. U.S. Patent 4,966,972, 1990, pp. 1-16.
19. Hessen, B.; Ringelberg, S. N.; Meppelder, G.; Teuben, J. H. Polym. Prepr. 2000, 41, 397-398.
20. Cockerton, B. R.; Deeming, A. J. J. Organomet. Chem. 1992, 426, C36-C39.
21. Akther, J.; Azam, K. A.; Das, A. R.; Hursthouse, M. B.; Kabir, S. E.; Abdul Malik, K. M.; Rosenberg, E.; Tesmer, M.; Vahrenkamp, H. J. Organomet. Chem. 1999, 588, 211-221.
22. Bradley, D. C.; Mehrotra, R. C.; Rothwell, I. P.; Singh, A. Alkoxo and Aryloxo Derivatives of Metals; Academic Press: London, 2001; and references therein.
23. Rothwell, I. P. Acc. Chem. Res. 1988, 21, 153-159.
24. Chamberlain, L.; Rothwell, I. P. J. Am. Chem. Soc. 1982, 104, 7338-7340.
25. Chamberlain, L. R.; Rothwell, A. P.; Rothwell, I. P. J. Am. Chem. Soc. 1984, 106, 1847-1848.
26. Chamberlain, L. R.; Rothwell, I. P.; Huffman, J. C. J. Am. Chem. Soc. 1986, 108, 1502-1509.
27. Vilardo, J. S.; Lockwood, M. A.; Hanson, L. G.; Clark, J. R.; Parkin, B. C.; Fanwick, P. E.; Rothwell, I. P. J. Chem. Soc., Dalton Trans. 1997, 3353-3362.
28. Steffey, B. D.; Chamberlain, L. R.; Chesnut, R. W.; Chebi, D. E.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1989, 8, 1419-1423.
29. Laplaza, C. E.; Cummins, C. C. Science 1995, 268, 861-863.
30. Cummins, C. C. Prog. Inorg. Chem. 1998, 47, 685-836, and references therein.
31. Cummins, C. C. Chem. Commun. 1998, 1777-1786, and references therein.
32. Farcasiu, D. Synthesis 1972, 615-616.
33. This reaction is presumably initiated by 1,2-hydride migration to give a complexed aldehyde prior to C-C bond formation. For a list of reagents that will induce this rearrangement, see: Larock, R. C. In Comprehensive Organic Transformations; VCH: New York, 1989; p 628.
34. Schrock, R. R.; Sharp, P. R. J. Am. Chem. Soc. 1978, 100, 2389-2399.
35. Bonanno, J. B.; Wolczanski, P. T.; Lobkovsky, E. B. J. Am. Chem. Soc. 1994, 116, 11159-11160.
36. Bonanno, J. B.; Henry, T. P.; Neithamer, D. R.; Wolczanski, P. T. J. Am. Chem. Soc. 1996, 118, 5132-5133.
37. Weller, K. J.; Gray, S. D.; Briggs, P. M.; Wigley, D. E. Organometallics 1995, 14, 5588-5597.
38. Castellano, B.; Solari, E.; Floriani, C.; Re, N.; Chiesi-Villa, A.; Rizzoli, C. Chem. Eur. J. 1999, 5, 722-737.
39. Another possibility suggested by a reviewer involves direct coupling of two coordinated pyridines followed by subsequent loss of dihydrogen, obviating the requirement for C-H activation at Ta occurring and an intermediate such as 5a being formed.
40. Diaconescu, P. L.; Cummins, C. C. J. Am. Chem. Soc. 2002, 124, 7660-7661.
41. Pangborn, A. M.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520.