Rhenium-catalyzed formation of indene frameworks via C-H bond activation: [3+2] Annulation of aromatic aldimines and acetylenes

Journal of the American Chemical Society

Volumn 127, Issue 39, 2005, Pages 13498-13499

  Kuninobu, Yoichiro ^a   Kawata, Atsushi ^a   Takai, Kazuhiko ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ALDIMINE DERIVATIVE; IMINE; INDENE DERIVATIVE; RHENIUM COMPLEX; TOLUENE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CATALYST; CHEMICAL BOND; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 26044451878     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0528174     Document Type: Article

References (33)

1. (a) Akbulut, U.; Khurshid, A. Hacioǧlu, B.; Toppare, L. Polymer 1990, 31, 1343.
2. (b) Barberá, J.; Rakitin, O. A.; Ros, M. B.; Torroba, T. Angew. Chem., Int. Ed. 1998, 37, 296.
3. (c) Yang, J.; Lakshmikanthan, M. V.; Cava, M. P.; Lorcy, D.; Bethelot, J. R. J. Org. Chem. 2000, 65, 6739.
4. Korte, A.; Legros, J.; Bolm, C. Synlett 2004, 13, 2397 and references therein.
5. Miller, R. B.; Frincke, J. M. J. Org. Chem. 1980, 45, 5312.
6. (a) Cadierno, V.; Diez, J.; Pilar, G. M.; Gimeno, J.; Lastra, E. Coord. Chem. Rev. 1999, 193-195, 147.
7. (b) Zargarian, D. Coord. Chem. Rev. 2002, 233-234, 157.
8. (c) Leino, R.; Lehmus, P.; Lehtonen, A. Eur. J. Inorg. Chem. 2004, 3201.
9. (a) Semmelhack, M. F.; Ho, S.; Cohen, D.; Steigerwald, M.; Lee, M. C.; Lee, G.; Gilbert, A. M.; Wulff, W. D.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7108.
10. (b) Halterman, R. L.; Zhu, C. Tetrahedron Lett. 1999, 40, 7445.
11. (c) Romines, K. R.; Lovasz, K. D.; Mizsak, S. A.; Morris, J. K.; Seest, E. P.; Man, F.; Tulinsky, J.; Judge, T. M.; Gammill, R. B. J. Org. Chem. 1999, 64, 1733.
12. (d) Xi, Z.; Guo, R.; Mito, S.; Van, H.; Kanno, K.-i.; Nakajima, K.; Takahashi, T. J. Org. Chem. 2003, 68, 1252.
13. (e) Ming-Yuan, L.; Madhushaw, R. J.; Liu, R.-S. J. Org. Chem. 2004, 69, 7700.
14. (f) Chang, K.J.; Rayabarapu, D. K.; Cheng, C.-H. J. Org. Chem. 2004, 69, 4781.
15. (g) Lautens, M.; Marquardt, T. J. Org. Chem. 2004, 69, 4607.
16. (a) Liebeskind, L. S.; Gasdaska, J. R.; McCallum, J. S. J. Org. Chem. 1989, 54, 669.
17. (b) Robinson, N. P.; Main, L.; Nicholson, B. K. J. Organomet. Chem. 1989, 364, C37.
18. (a) Kakiuchi, F.; Murai, S. Top. Organomet. Chem. 1999, 3, 47.
19. (b) Guari, Y.; Sabo-Etienne, S.; Chaudret, B. Eur. J. Inorg. Chem. 1999, 1047.
20. (c) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698.
21. (d) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
22. 1H NMR yields were determined by using 1,1,2,2-tetrachloroethane as an internal standard.
23. A detailed structure of the indene framework was determined by X-ray crystal structure analysis. See the Supporting Information.
24. Heat and/or a rhenium catalyst promote interconversion of substituents at the 1,2-position of the indene framework, though the mechanism is not clear yet.
25. Kakiuchi, F.; Sato, T.; Tsujimoto, T.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1998, 1053.
26. 3.
27. 2, 35% (17:83); THF, 17% (<1:>99); DMI, 17% (41:59); DMF, <1%.
28. 5, see: (a) Böhm, A.; Sünkel, K.; Polborn, K.; Beck, W. J. Organomet. Chem. 1998, 552, 237.
29. 2Ph)(CO),. see: (b) Djukic, J.-P.; Maisse, A.; Pfeffer, M.; Dötz, K. H.; Nieger, M. Organometallics 1999, 18, 2786.
30. 2 with aldimine, we could not observe the formation of the intermediate.
31. 3 or tributylamine) and noticed that the reaction with the base proceeded without decreasing the yield. Thus, we are tempted to assume that the rhenium-catalyzed reaction proceeds via the C-H bond activation.
32. Jacob, J.; Espenson, J. H. Inorg. Chim. Acta 1998, 270, 55.
33. 3)-H bond activation has been reported: Chen, H.; Hartwig, J. F. Angew. Chem., Int. Ed. 1999, 38, 3391.