Regioselective Synthesis of Substituted Naphthalenes: A Novel de Novo Approach Based on a Metal-Free Protocol for Stepwise Cycloaddition of o-Alkynylbenzaldehyde Derivatives with Either Alkynes or Alkenes

Organic Letters

Volumn 5, Issue 22, 2003, Pages 4121-4123

  Barluenga, José ^a   Vázquez Villa, Henar ^a   Ballesteros, Alfredo ^a   González, José M ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYL GROUP; BENZALDEHYDE DERIVATIVE; NAPHTHALENE DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION; CYCLOADDITION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0344082894     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035691t     Document Type: Article

References (24)

1. For recent examples, see: (a) Yasukawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 12680. (b) Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650. (c) Viswanathan, G. S.; Wang, M.; Li, C.-J. Angew. Chem., Int. Ed. 2002, 41, 2138. (d) Huang, Q. ; Larock, R. C. Org. Lett. 2002, 4, 2505. (e) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518.
2. For recent examples, see: (a) Yasukawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 12680. (b) Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650. (c) Viswanathan, G. S.; Wang, M.; Li, C.-J. Angew. Chem., Int. Ed. 2002, 41, 2138. (d) Huang, Q. ; Larock, R. C. Org. Lett. 2002, 4, 2505. (e) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518.
3. For recent examples, see: (a) Yasukawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 12680. (b) Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650. (c) Viswanathan, G. S.; Wang, M.; Li, C.-J. Angew. Chem., Int. Ed. 2002, 41, 2138. (d) Huang, Q. ; Larock, R. C. Org. Lett. 2002, 4, 2505. (e) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518.
4. For recent examples, see: (a) Yasukawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 12680. (b) Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650. (c) Viswanathan, G. S.; Wang, M.; Li, C.-J. Angew. Chem., Int. Ed. 2002, 41, 2138. (d) Huang, Q. ; Larock, R. C. Org. Lett. 2002, 4, 2505. (e) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518.
5. For recent examples, see: (a) Yasukawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 12680. (b) Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650. (c) Viswanathan, G. S.; Wang, M.; Li, C.-J. Angew. Chem., Int. Ed. 2002, 41, 2138. (d) Huang, Q. ; Larock, R. C. Org. Lett. 2002, 4, 2505. (e) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518.
6. To this aim, not only organometallic transformations but also thermally and photochemically driven reactions have been reported. For illustrative examples, see: (a) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Org. Chem. 2003, 68, 1938. (b) Takahashi, T.; Li, Y.; Stepnicka, P.; Kitamura, M.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124, 576. (c) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Am. Chem. Soc. 2001, 123, 9178. (d) Bowles, D. M.; Anthony, J. E. Org. Lett. 2000, 2, 85. (e) Yoshikawa, E.; Yamamoto, Y. Angew. Chem., Int. Ed. 2000, 39, 173. (f) Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Am. Chem. Soc. 1999, 121, 5827. (f) de Frutos, Ó.; Echavarren, A. M. Tetrahedron Lett. 1997, 38, 7941. (g) Takahashi, T.; Hara, R.; Nishihara, Y.; Kotora, M. J. Am. Chem. Soc. 1996, 118, 5154. (h) Bradford, C.; Fleming, S. A.; Ward, S. C. Tetrahedron Lett. 1995, 36, 4189.
7. To this aim, not only organometallic transformations but also thermally and photochemically driven reactions have been reported. For illustrative examples, see: (a) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Org. Chem. 2003, 68, 1938. (b) Takahashi, T.; Li, Y.; Stepnicka, P.; Kitamura, M.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124, 576. (c) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Am. Chem. Soc. 2001, 123, 9178. (d) Bowles, D. M.; Anthony, J. E. Org. Lett. 2000, 2, 85. (e) Yoshikawa, E.; Yamamoto, Y. Angew. Chem., Int. Ed. 2000, 39, 173. (f) Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Am. Chem. Soc. 1999, 121, 5827. (f) de Frutos, Ó.; Echavarren, A. M. Tetrahedron Lett. 1997, 38, 7941. (g) Takahashi, T.; Hara, R.; Nishihara, Y.; Kotora, M. J. Am. Chem. Soc. 1996, 118, 5154. (h) Bradford, C.; Fleming, S. A.; Ward, S. C. Tetrahedron Lett. 1995, 36, 4189.
8. To this aim, not only organometallic transformations but also thermally and photochemically driven reactions have been reported. For illustrative examples, see: (a) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Org. Chem. 2003, 68, 1938. (b) Takahashi, T.; Li, Y.; Stepnicka, P.; Kitamura, M.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124, 576. (c) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Am. Chem. Soc. 2001, 123, 9178. (d) Bowles, D. M.; Anthony, J. E. Org. Lett. 2000, 2, 85. (e) Yoshikawa, E.; Yamamoto, Y. Angew. Chem., Int. Ed. 2000, 39, 173. (f) Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Am. Chem. Soc. 1999, 121, 5827. (f) de Frutos, Ó.; Echavarren, A. M. Tetrahedron Lett. 1997, 38, 7941. (g) Takahashi, T.; Hara, R.; Nishihara, Y.; Kotora, M. J. Am. Chem. Soc. 1996, 118, 5154. (h) Bradford, C.; Fleming, S. A.; Ward, S. C. Tetrahedron Lett. 1995, 36, 4189.
9. To this aim, not only organometallic transformations but also thermally and photochemically driven reactions have been reported. For illustrative examples, see: (a) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Org. Chem. 2003, 68, 1938. (b) Takahashi, T.; Li, Y.; Stepnicka, P.; Kitamura, M.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124, 576. (c) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Am. Chem. Soc. 2001, 123, 9178. (d) Bowles, D. M.; Anthony, J. E. Org. Lett. 2000, 2, 85. (e) Yoshikawa, E.; Yamamoto, Y. Angew. Chem., Int. Ed. 2000, 39, 173. (f) Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Am. Chem. Soc. 1999, 121, 5827. (f) de Frutos, Ó.; Echavarren, A. M. Tetrahedron Lett. 1997, 38, 7941. (g) Takahashi, T.; Hara, R.; Nishihara, Y.; Kotora, M. J. Am. Chem. Soc. 1996, 118, 5154. (h) Bradford, C.; Fleming, S. A.; Ward, S. C. Tetrahedron Lett. 1995, 36, 4189.
10. To this aim, not only organometallic transformations but also thermally and photochemically driven reactions have been reported. For illustrative examples, see: (a) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Org. Chem. 2003, 68, 1938. (b) Takahashi, T.; Li, Y.; Stepnicka, P.; Kitamura, M.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124, 576. (c) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Am. Chem. Soc. 2001, 123, 9178. (d) Bowles, D. M.; Anthony, J. E. Org. Lett. 2000, 2, 85. (e) Yoshikawa, E.; Yamamoto, Y. Angew. Chem., Int. Ed. 2000, 39, 173. (f) Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Am. Chem. Soc. 1999, 121, 5827. (f) de Frutos, Ó.; Echavarren, A. M. Tetrahedron Lett. 1997, 38, 7941. (g) Takahashi, T.; Hara, R.; Nishihara, Y.; Kotora, M. J. Am. Chem. Soc. 1996, 118, 5154. (h) Bradford, C.; Fleming, S. A.; Ward, S. C. Tetrahedron Lett. 1995, 36, 4189.
11. To this aim, not only organometallic transformations but also thermally and photochemically driven reactions have been reported. For illustrative examples, see: (a) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Org. Chem. 2003, 68, 1938. (b) Takahashi, T.; Li, Y.; Stepnicka, P.; Kitamura, M.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124, 576. (c) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Am. Chem. Soc. 2001, 123, 9178. (d) Bowles, D. M.; Anthony, J. E. Org. Lett. 2000, 2, 85. (e) Yoshikawa, E.; Yamamoto, Y. Angew. Chem., Int. Ed. 2000, 39, 173. (f) Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Am. Chem. Soc. 1999, 121, 5827. (f) de Frutos, Ó.; Echavarren, A. M. Tetrahedron Lett. 1997, 38, 7941. (g) Takahashi, T.; Hara, R.; Nishihara, Y.; Kotora, M. J. Am. Chem. Soc. 1996, 118, 5154. (h) Bradford, C.; Fleming, S. A.; Ward, S. C. Tetrahedron Lett. 1995, 36, 4189.
12. To this aim, not only organometallic transformations but also thermally and photochemically driven reactions have been reported. For illustrative examples, see: (a) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Org. Chem. 2003, 68, 1938. (b) Takahashi, T.; Li, Y.; Stepnicka, P.; Kitamura, M.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124, 576. (c) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Am. Chem. Soc. 2001, 123, 9178. (d) Bowles, D. M.; Anthony, J. E. Org. Lett. 2000, 2, 85. (e) Yoshikawa, E.; Yamamoto, Y. Angew. Chem., Int. Ed. 2000, 39, 173. (f) Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Am. Chem. Soc. 1999, 121, 5827. (f) de Frutos, Ó.; Echavarren, A. M. Tetrahedron Lett. 1997, 38, 7941. (g) Takahashi, T.; Hara, R.; Nishihara, Y.; Kotora, M. J. Am. Chem. Soc. 1996, 118, 5154. (h) Bradford, C.; Fleming, S. A.; Ward, S. C. Tetrahedron Lett. 1995, 36, 4189.
13. To this aim, not only organometallic transformations but also thermally and photochemically driven reactions have been reported. For illustrative examples, see: (a) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Org. Chem. 2003, 68, 1938. (b) Takahashi, T.; Li, Y.; Stepnicka, P.; Kitamura, M.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124, 576. (c) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Am. Chem. Soc. 2001, 123, 9178. (d) Bowles, D. M.; Anthony, J. E. Org. Lett. 2000, 2, 85. (e) Yoshikawa, E.; Yamamoto, Y. Angew. Chem., Int. Ed. 2000, 39, 173. (f) Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Am. Chem. Soc. 1999, 121, 5827. (f) de Frutos, Ó.; Echavarren, A. M. Tetrahedron Lett. 1997, 38, 7941. (g) Takahashi, T.; Hara, R.; Nishihara, Y.; Kotora, M. J. Am. Chem. Soc. 1996, 118, 5154. (h) Bradford, C.; Fleming, S. A.; Ward, S. C. Tetrahedron Lett. 1995, 36, 4189.
14. To this aim, not only organometallic transformations but also thermally and photochemically driven reactions have been reported. For illustrative examples, see: (a) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Org. Chem. 2003, 68, 1938. (b) Takahashi, T.; Li, Y.; Stepnicka, P.; Kitamura, M.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124, 576. (c) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Am. Chem. Soc. 2001, 123, 9178. (d) Bowles, D. M.; Anthony, J. E. Org. Lett. 2000, 2, 85. (e) Yoshikawa, E.; Yamamoto, Y. Angew. Chem., Int. Ed. 2000, 39, 173. (f) Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Am. Chem. Soc. 1999, 121, 5827. (f) de Frutos, Ó.; Echavarren, A. M. Tetrahedron Lett. 1997, 38, 7941. (g) Takahashi, T.; Hara, R.; Nishihara, Y.; Kotora, M. J. Am. Chem. Soc. 1996, 118, 5154. (h) Bradford, C.; Fleming, S. A.; Ward, S. C. Tetrahedron Lett. 1995, 36, 4189.
15. Barluenga, J.; Vázquez-Villa, H.; Ballesteros, A.; González, J. M. J. Am. Chem. Soc. 2003, 125, 9028.
16. For a recent synthetic application of this commercially available reagent, see: Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406.
17. The structures for compounds 3 and 4 are based on their spectroscopic and analytical data. For the case of 3d and 3e, 2D-NMR experiments (HMBC) confirmed the depicted structures (see Supporting Information). For compounds 4, satisfactory comparison with already published data was possible for some compounds (see characterization data in ref 1b).
18. See for instance: Barluenga, J.; Campos, P. J.; González, J. M.; Suárez, J. L.; Asensio, G. J. Org. Chem. 1991, 56, 2234.
19. No evidences for the formation of other regioisomers of compound 3 were obtained from GC analysis of crude reaction mixtures.
20. (a) Barluenga, J.; Rodríguez, M. A.; Campos, P. J. J. Org. Chem. 1990, 55, 3104.
21. (b) Barluenga, J.; Llorente, I.; Alvarez-García, L. J.; González, J. M.; Campos, P. J.; Díaz, M. R.; García-Granda, S. J. Am. Chem. Soc. 1997, 119, 6933.
22. (c) See also ref 3.
23. For related intermediate species triggered by gold salts instead of iodonium ions, see ref 1b.
24. For the chemistry of this class of compounds, see: Kuznetsov, E.; Shcherbakova, I. V.; Balaban, A. T. Adv. Heterocycl. Chem. 1990, 50, 157.