Totally chemo- and regioselective cobalt(I)-mediated formal intermolecular cyclotrimerization of alkynes

Organic Letters

Volumn 6, Issue 9, 2004, Pages 1519-1521

  Chouraqui, Gaëlle ^a   Petit, Marc ^a   Aubert, Corinne ^a   Malacria, Max ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; COBALT COMPLEX; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SILICON DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; CYCLOTRIMERIZATION; SILYLATION; SUBSTITUTION REACTION;

EID: 2442551867     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049484k     Document Type: Article

References (33)

1. For reviews. see: (a) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette. L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1129-1162. (b) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Hegedus, L., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, pp 741-770. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662.
2. For reviews. see: (a) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette. L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1129-1162. (b) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Hegedus, L., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, pp 741-770. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662.
3. For reviews. see: (a) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette. L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1129-1162. (b) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Hegedus, L., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, pp 741-770. (c) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662.
4. For reviews. see: (a) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette. L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1129-1162. (b) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Hegedus, L., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, pp 741-770. (c) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662.
5. (e) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901-2915.
6. (f) Malacria, M.; Aubert, C.; Renaud, J. L. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Lautens, M., Trost, B. M., Eds.; Georg Thieme Verlag: Stuttgart, 2001; Vol. 1. pp 439-530.
7. (a) Ozerov, O. V.; Patrick, B. O.; Ladipo, F. T. J. Am. Chem. Soc. 2000, 122, 6423-6431.
8. (b) Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672-1680.
9. (c) Takahashi, T. Pure Appl. Chem. 2001, 73, 271-274.
10. (d) Saito, S.; Kawasaki, T.; Tsuboya, N.; Yamamoto, Y. J. Org. Chem. 2001, 66, 796-802.
11. (e) Mori, N.; Ikeda, S.-i.; Odashima, K. Chem. Commun. 2001, 181-182.
12. (f) Sato, Y.; Ohashi, K.; Mori, M. Tetrahedron Lett. 1999, 40, 5231-5234.
13. (g) Sakurai, H.; Nakadaira, Y.; Hosomi, A.; Eriyama, Y.; Hirama, K.; Kabuto, C. J. Am. Chem. Soc. 1984, 106, 8315-8316.
14. (h) Tanaka, K.; Shirasaka, K. Org. Lett. 2003, 5, 4697-4699 and references therein.
15. (a) Wakatsuki, Y.; Kuramitsu, T.; Yamazaki, H. Tetrahedron Lett. 1974, 4549-4552.
16. (b) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 536-556.
17. (c) Vollhardt, K. P. C. Pure Appl. Chem. 1985, 57, 1819-1826.
18. (d) Slowinski, F.; Aubert, C.; Malacria, M. Adv. Synth. Catal. 2001, 343, 64-67.
19. (e) Petit, M.; Chouraqui, G.: Phansavath, P.; Aubert, C.; Malacria, M. Org. Lett. 2002, 4, 1027-1029.
20. (f) Yamamoto, Y.; Arakawa, T.; Ogawa, R.; Itoh, K. J. Am. Chem. Soc. 2003, 125, 12143-12160 and references therein.
21. (a) Gevorgyan, V.; Radhakrishnan, U.: Takeda, A.; Rubina, M.; Rubin, M.; Yamamoto, Y. J. Org. Chem. 2001, 66, 2835-2841.
22. (b) Rubin, M.; Sromek, A. W.: Gevorgyan, V. Synlett 2003, 2265-2291.
23. For reviews, see: (a) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (b) Fensterbank, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. Gauthier, D. R. J.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289-2338. White, J. D.; Carter, R. G. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Fleming, I., Ed.; Georg Thieme Verlag: Stuttgart, 2001; Vol. 4, pp 371-412. (e) Skrydstrup, T. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Fleming, I., Ed.; Georg Thieme Verlag: Stuttgart, 2001; Vol. 4, pp 439-530.
24. For reviews, see: (a) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (b) Fensterbank, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. Gauthier, D. R. J.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289-2338. White, J. D.; Carter, R. G. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Fleming, I., Ed.; Georg Thieme Verlag: Stuttgart, 2001; Vol. 4, pp 371-412. (e) Skrydstrup, T. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Fleming, I., Ed.; Georg Thieme Verlag: Stuttgart, 2001; Vol. 4, pp 439-530.
25. For reviews, see: (a) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (b) Fensterbank, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (c) Gauthier, D. R. J.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289-2338. White, J. D.; Carter, R. G. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Fleming, I., Ed.; Georg Thieme Verlag: Stuttgart, 2001; Vol. 4, pp 371-412. (e) Skrydstrup, T. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Fleming, I., Ed.; Georg Thieme Verlag: Stuttgart, 2001; Vol. 4, pp 439-530.
26. For reviews, see: (a) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (b) Fensterbank, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (c) Gauthier, D. R. J.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289-2338. (d) White, J. D.; Carter, R. G. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Fleming, I., Ed.; Georg Thieme Verlag: Stuttgart, 2001; Vol. 4, pp 371-412. (e) Skrydstrup, T. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Fleming, I., Ed.; Georg Thieme Verlag: Stuttgart, 2001; Vol. 4, pp 439-530.
27. For reviews, see: (a) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277. (b) Fensterbank, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. (c) Gauthier, D. R. J.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289-2338. (d) White, J. D.; Carter, R. G. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Fleming, I., Ed.; Georg Thieme Verlag: Stuttgart, 2001; Vol. 4, pp 371-412. (e) Skrydstrup, T. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Fleming, I., Ed.; Georg Thieme Verlag: Stuttgart, 2001; Vol. 4, pp 439-530.
28. Brummond, K. M.; Sill, P. C.; Rickards, B.; Geib, S. J. Tetrahedron Lett. 2002, 43, 3755-3738.
29. (a) Chang, S.; Grubbs, R. H. Tetrahedron Lett. 1997, 38, 4757-4760. Van de Weghe, P.; Aoun, D.; Boiteau, J. G.; Eustache, J. Org. Lett. 2002, 4, 4105-4108 and pertinent references therein.
30. (a) Chang, S.; Grubbs, R. H. Tetrahedron Lett. 1997, 38, 4757-4760. Van de Weghe, P.; Aoun, D.; Boiteau, J. G.; Eustache, J. Org. Lett. 2002, 4, 4105-4108 and pertinent references therein.
31. Eckenberg, P.; Groth, U. Synlett 2003, 2188-2192.
32. Petit, M.; Chouraqui, G.; Aubert, C.; Malacria, M. Org. Lett. 2003, 5, 2037-2040.
33. Compound 4 was used without further purification in the next step; see Scheme 4.