Lewis acid stabilized methylidene and oxoscandium complexes

Journal of the American Chemical Society

Volumn 130, Issue 44, 2008, Pages 14438-14439

  Scott, Jennifer ^a   Fan, Hongjun ^a   Wicker, Benjamin F ^a   Fout, Alison R ^a   Baik, Mu Hyun ^a   Mindiola, Daniel J ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LEWIS ACID; METHYLIDENE COMPLEX; OXOSCANDIUM COMPLEX; SCANDIUM; SCANDIUM METHYLIDENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ROOM TEMPERATURE; SOLID STATE; X RAY DIFFRACTION;

EID: 55549084253     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja806635x     Document Type: Article

References (35)

1. Tebbe, F. N.; Parshall, G. W.; Ovenall, D. W. J. Am. Chem. Soc. 1979, 101, 5074.
2. For seminal examples:(a) Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611.
3. (b) Petasis, N. A.; Hu, Y.-H. Curr. Org. Chem. 1997, 1, 249.
4. (c) Petasis, N. A.; Hu, Y.-H. J. Org. Chem. 1997, 62, 782.
5. (d) Petasis, N. A.; Lu, S.-P.; Bzowej, E. I.; Fu, D.-K.; Staszewski, J. P.; Akritopoulou-Zanze, I.; Patane, M. A.; Hu, Y.-H. Pure Appl. Chem. 1996, 68, 667.
6. (e) Pine, S. H. Org. React. 1993, 43, 1.
7. (f) Cannizzo, L. F.; Grubbs, R. H. J. Org. Chem. 1985, 50, 2386-2387.
8. (a) Fürstner, A. Adv. Synth. Catal. 2002, 344, 567.
9. (b) Schrock, R. R. Adv. Synth. Catal. 2002, 344, 571.
10. (c) Schrock, R. R. Chem. Rev. 2002, 102, 145.
11. (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
12. (e) Grubbs, R. H. Adv. Synth. Catal. 2007, 349, 34.
13. (f) Schrock, R. R. Adv. Synth. Catal. 2007, 349, 41.
14. Ott, K. C.; deBoer, E. J. M.; Grubbs, R. H. Organometallics 1984, 3, 223.
15. Schrock, R. R.; Sharp, P. R. J. Am. Chem. Soc. 1978, 100, 2389.
16. Giesbrecht, G. R.; Gordon, J. C. Dalton Trans. 2004, 2387.
17. (a) Dietrich, H. M.; Törnroos, K. W.; Anwander, R. J. Am. Chem. Soc. 2006, 128, 9298.
18. (b) Masuda, J. D.; Jantunen, K. C.; Ozerov, O. V.; Noonan, K. J. T.; Gates, D. P.; Scott, B. L.; Kiplinger, J. L. J. Am. Chem. Soc. 2008, 130, 2408.
19. (c) Schumann, H.; Muller, J. J. Organomet. Chem. 1979, 169, C1.
20. (a) Aparna, K.; Ferguson, M.; Cavell, R. G. J. Am. Chem. Soc. 2000, 122, 726.
21. (b) Cavell, R. G.; Babu, R. P. K.; Aparna, K. J. Organomet. Chem. 2001, 617, 158.
22. (c) Liddle, S. T.; McMaster, J.; Green, J. C.; Arnold, P. L. Chem. Commun. 2008, 1747.
23. Scott, J.; Basuli, F.; Fout, A. R.; Huffman, J. C.; Mindiola, D. J. Angew. Chem., Int. Ed., 2008, http://dx.doi.org/anie.200803325.
24. A similar pincer analogue of scandium has been reported. (a) Fryzuk, M. D.; Giesbrecht, G.; Rettig, S. J. Organometallics 1996, 15, 3329.
25. (b) Fryzuk, M. D.; Giesbrecht, G. R.; Rettig, S. J. Can. J. Chem. 2000, 78, 1003.
26. See Supporting Information.
27. 2 has been reported for Zr(IV). (a) von H. Spence, R. E.; Parks, D. J.; Piers, W. E.; MacDonald, M.-A.; Zaworotko, M. J.; Steven J. Rettig, S. J. Angew, Chem. Int. Ed. 1995, 34, 1230. A Sc methylidene has been proposed along a Lewis acid promoted cyclometallation pathway.
28. (b) Conroy, K. D.; Hayes, P. G.; Piers, W. E.; Parvez, M. Organometallics 2007, 26, 4464.
29. (a) Thompson, M. E.; Baxter, S. M.; Bulls, A. R.; Burger, B. J.; Nolan, M. C.; Santarsiero, B. D.; Schaefer, W. P.; Bercaw, J. E. J. Am. Chem. Soc. 1987, 109, 203.
30. (b) Hayes, P. G.; Piers, W. E.; McDonald, R. J. Am. Chem. Soc. 2002, 124, 2132.
31. (c) Piers, W. E.; D; Emslie, D. J. H. Coord. Chem. Rev. 2002, 233.
32. (d) Mountford, P.; Ward, B. D. Chem. Commun. 2003, 1797.
33. The bonding in a pentacoordinate methylidene carbon has been investigated theoretically. Radius, U.; Silverio, S. J.; Hoffmann, R.; Gleiter, R. Organometallics 1996, 15, 3737.
34. Adam, W.; Baeza, J.; Liu, J.-C. J. Am. Chem. Soc. 1972, 94, 2000.
35. Bond lengths were obtained from the Cambridge Structural Database.