AuBr3-catalyzed [4 + 2] benzannulation between an enynal unit and enol

Journal of the American Chemical Society

Volumn 126, Issue 24, 2004, Pages 7458-7459

  Asao, Naoki ^a   Aikawa, Haruo ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE; GOLD;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; SYNTHESIS;

ALDEHYDES; ALKYNES; BENZALDEHYDES; BROMIDES; CATALYSIS; CYCLIZATION; GOLD; KETONES; MOLECULAR STRUCTURE;

EID: 2942682670     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0477367     Document Type: Article

References (35)

1. For example, see: Fringuelli, F.; Taticchi, A. The Diels-Alder Reaction - Selected Practical Methods; Wiley: Chichester, 2002.
2. Enol ethers, including furan derivatives, are known to behave as 2π systems. For example, see: (a) Chen, C.-H.; Rao, P. D.; Liao, C.-C. J. Am. Chem. Soc. 1998, 120, 13254-13255.
3. (b) Avalos, M.; Babiano, R.; Cabello, N.; Cintas, P.; Hursthouse, M. B.; Jiménez, J. L.; Light, M. E.; Palacios, J. C. J. Org. Chem. 2003, 68, 7193-7203.
4. Asao, N.; Kasahara, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2003, 42, 3504-3506.
5. (a) Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650-12651.
6. (b) Asao, N.; Nogami, T.; Lee, S.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 10921-10925.
7. For reviews, see: (a) Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, 2002.
8. (b) de Koning, C. B.; Rousseau, A.; van Otterlo, W. A. L. Tetrahedron 2003, 59, 7-36.
9. (c) Katritzky, A. R.; Li, J.; Xie, L. Tetrahedron 1999, 55, 8263-8293.
10. For recent examples for naphthalene syntheses, see: (a) Dyker, G.; Stirner, W.; Henkel, G.; Kockerling, M. Tetrahedron Lett. 1999, 40, 7457-7458.
11. (b) Iwasawa, N.; Shido, M.; Maeyama. K.; Kusama, H. J. Am. Chem. Soc. 2000, 122, 10226-10227.
12. (c) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518-519.
13. (d) Huang, Q.; Larock, R. C. Org. Lett. 2002, 4, 2505-2508.
14. (e) Viswanathan, G. S.; Wang, M.; Li, C.-J. Angew. Chem., Int. Ed. 2002, 41, 2138-2141.
15. (f) Yasukawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 12680-12681.
16. (g) Ramakrshna, T. V. V.; Sharp, P. R. Org. Lett. 2003, 5, 877-879.
17. (h) Barluenga, J.; Vazquez-Villa, H.; Ballesteros, A.; Gonzalez, J. M. Org. Lett. 2003, 5, 4121-4123.
18. (i) Shen, H.-C.; Pal, S.; Lian, J.-J.; Liu, R.-S. J. Am. Chem. Soc. 2003, 125, 15762-15763.
19. (j) Kusama, H.; Funami, H.; Takaya, J.; Iwasawa, N. Org. Lett. 2004, 6, 605-608.
20. 2-catalyzed reaction of 1a with 4a was conducted in THF, we could not detect the formation of 2a as an intermediate.
21. For reviews on the gold catalyst, see: (a) Dyker, G. Angew. Chem., Int. Ed. 2000, 39, 4237-4239.
22. (b) Hashmi, A. S. K. Gold Bull. 2003, 36, 3-9.
23. Gold-catalyzed benzannulation, see: (a) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553-11554.
24. (b) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. Org. Lett. 2001, 3, 3769-3771.
25. (c) Dankwardt, J. W. Tetrahedron Lett. 2001, 42, 5809-5812.
26. (d) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. Catal. Today 2002, 72, 19-27.
27. For recent benzannulation using enynals, see: (a) Ohe, K.; Miki, K.; Yokoi, T.; Nishino, F.; Uemura, S. Organometallics 2000, 19, 5525-5528.
28. (b) Miki, K.; Yokoi, T.; Nishino, F.; Ohe, K.; Uemura, S. J. Organomet. Chem. 2002, 645, 228-234.
29. (c) Ohe, K.; Yokoi, T.; Miki, K.; Nishino, F.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 526-527.
30. Acid-induced pyrylium salts syntheses by electrophilic cyclizations of o-alkynyl(oxo)benzenes, see: (a) Tovar, J. D.; Swager, T. M. J. Org. Chem. 1999, 64, 6499-6504.
31. (b) Barluenga, J.; Vázquez-Villa, H.; Ballesteros, A.; González, J. M. J. Am. Chem. Soc. 2003, 125, 9028-9029.
32. (c) Zhu, J.; Germain. A. R.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2004, 43, 1239-1243.
33. Benzo[c]pyrylium salts are known to play a dien part in the Diels-Alder reaction with ethyl vinyl ether and azomethines, see: Kuznetsov, E.; Shcherbakova, I. V.; Balaban, A. T. Adv. Heterocycl. Chem. 1990, 50, 157-254.
34. 3 in water, might promote the enolization process, see: Dyker, G.; Hildebrandt, D.; Liu, J.; Merz, K. Angew. Chem., Int. Ed. 2003, 42, 4399-4402.
35. A theoretical study on keto-enol tautomerization was reported, see: Lee, D.; Kim, C. K.; Lee, B.-S.; Lee, I.; Lee, B. C. J. Comput. Chem. 1997, 18, 56-69 and references therein.