Understanding the formation of N-H tautomers from α-substituted pyridines: Tautomerization of 2-ethylpyridine promoted by osmium

Journal of the American Chemical Society

Volumn 129, Issue 36, 2007, Pages 10998-10999

  Buil, María L ^a   Esteruelas, Miguel A ^a   Garcés, Karin ^a   Oliván, Montserrat ^a   Oñate, Enrique ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ETHIONAMIDE; KETONE DERIVATIVE; OSMIUM; PYRIDINE DERIVATIVE; RUTHENIUM;

ADDITION REACTION; ALKYLATION; ARTICLE; CATALYST; CHEMICAL REACTION;

EID: 34548738299     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja073673r     Document Type: Article

References (39)

1. Ashworth, M. R. F.; Daffern, R. P.; Hammick. D. L. J. Chem. Soc. 1939, 809.
2. Lavorato, D.; Terlouw, J. K.; Dargel, T. K.; Koch, W.; McGibbon, G. A.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 11898.
3. Alvarez, E.; Conejero, S.; Paneque, M.; Petronilho, A.; Poveda, M. L.; Serrano, O.; Carmona, E. J. Am. Chem. Soc. 2006, 128, 13060.
4. Esteruelas, M. A.; Fernández-Alvarez, F. J.; Oñate, E. J. Am. Chem. Soc. 2006, 128, 13044.
5. Burling, S.; Mahon, M. F.; Powell, R. E.; Whittlesey, M. K.; Williams, J. M. J. J. Am. Chem. Soc. 2006, 128, 13702.
6. Sini, G.; Eisenstein, O.; Crabtree, R. H. Inorg. Chem. 2002, 41, 602.
7. Kunz, D. Angew. Chem., Int. Ed. 2007, 46, 3405.
8. See for example: (a) Moore, E. J.; Pretzer, W. R.; O'Connell, T. J.; Harris, J.; LaBounty, L.; Chou, L.; Grimmer, S. S. J. Am. Chem. Soc. 1992, 114, 5888.
9. (b) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493.
10. (c) Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2006, 128, 5604.
11. (d) Wiedemann, S. H.; Lewis, J. C.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2006, 128, 2452.
12. Lewis, J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2007, 129, 5332.
13. Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
14. (a) Esteruelas, M. A.; Oro, L. A. Adv. Organomet. Chem. 2001, 47, 1.
15. (b) Esteruelas, M. A.; López, A. M. Organometallics 2005, 24, 3584.
16. (c) Esteruelas, M. A.; López, A. M.; Oliván, M. Coord. Chem. Rev. 2007, 251, 795.
17. (a) Barrio, P.; Castarlenas, R.; Esteruelas, M. A.; Lledós, A.; Maseras, F.; Oñate, E.; Tomàs, J. Organometallics 2001, 20, 442.
18. (b) Esteruelas, M. A.; Lledós, A.; Oliván, M.; Oñate, E.; Tajada, M. A.; Ujaque, G. Organometallics 2003, 22, 3753.
19. (c) Eguillor, B.; Esteruelas, M. A.; Oliván, M.; Oñate, E. Organometallics 2005, 24, 1428.
20. (d) Esteruelas, M. A.; Hernández, Y. A.; López, A. M.; Oliván, M.; Oñate, E. Organometallics 2005, 24, 5989.
21. Barrio, P.; Esteruelas, M. A.; Oñate, E. Organometallics 2004, 23, 3627.
22. 2 with 2-ethylpyridine under the same conditions as those used for promoting the tautomerization of quinoline and 8-methylquinoline leads to a complex mixture of products containing 2-vinylpyridine or metalated 2-vinylpyridine, resulting from the dehydrogenation of the ethyl group. Under those conditions tautomerization is not observed.
23. Cardone, R.; Taube, H. J. Am. Chem. Soc. 1987, 109, 8101.
24. (a) Raubenheimer, H. G.; Toerien, J. G.; Kruger, G. J.; Otte, R.; van Zyl, W.; Oliver, P. J. Organomet. Chem. 1994, 466, 291.
25. (b) Owen, J. S.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 2004, 126, 8247.
26. (c) Albrecht, M.; Stoeckli-Evans, H. Chem. Commun. 2005, 4705.
27. Barrio, P.; Esteruelas, M. A.; Lledós, A.; Oñate, E.; Tomás, J. Organometallics 2004, 23, 3008.
28. Sabo-Etienne, S.; Chaudret, B. Chem. Rev. 1998, 98, 2077.
29. (a) Barea, G.; Esteruelas, M. A.; Lledós, A.; López, A. M.; Oñate, E. Tolosa, J. I. Organometallics 1998, 17, 4065.
30. (b) Castarlenas, R. Esteruelas, M. A.; Gutiérrez-Puebla, E.; Jean, Y.; Lledós, A.; Martín, M. Tomás, J. Organometallics 1999, 18, 4296.
31. (c) Eguillor, B.; Esteruelas, M. A.; Oliván, M.; Oñate, E. Organometallics 2006, 25, 4691.
32. Jessop, P. G.; Morris, R. H. Coord. Chem. Rev. 1992, 121, 155.
33. (a) Castarlenas, R.; Esteruelas, M. A.; Oñate, E. Organometallics 2005, 24, 4343.
34. (b) Arnold, P. L.; Pearson, S. Coord. Chem. Rev. 2007, 251, 596.
35. (c) Castarlenas, R.; Esteruelas, M. A.; Oñate, E. Organometallics 2007, 26, 2129.
36. 4 formally resulting from the replacement of the heterocycle by acetonitrile in 2 is stable and has been characterized by X-ray diffraction analysis (see Supporting Information).
37. (a) Buil. M. L.; Esteruelas, M. A.; Oñate, E.; Ruiz, N. Organometallics 1998, 17, 3346.
38. (b) Esteruelas, M. A.; Gutiérrez-Puebla, E.; López, A. M.; Oñate, E ; Tolosa, J. I. Organometallics 2000, 19, 275.
39. + (R = Me, Ph) react in the same manner as 2 to give 3.