Fluorenes and styrenes by Au(I)-catalyzed annulation of enynes and alkynes

Journal of the American Chemical Society

Volumn 130, Issue 12, 2008, Pages 3736-3737

  Gorin, David J ^a   Watson, Iain D G ^a   Toste, F Dean ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; FLUORENE DERIVATIVE; STYRENE DERIVATIVE;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DIASTEREOISOMER; DIMERIZATION; MOLECULAR INTERACTION; OLEFINATION; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

ALKYNES; CATALYSIS; CYCLIZATION; FLUORENES; GOLD; MOLECULAR STRUCTURE; ORGANOGOLD COMPOUNDS; STEREOISOMERISM; STYRENES;

EID: 41149166160     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja710990d     Document Type: Article

References (40)

1. For a review, see: (a) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901.
2. Intramolecular annulation of enynes and alkynes: (b) Dunetz, J. R.; Danheiser, R. L. J. Am. Chem. Soc. 2005, 127, 5776.
3. (c) Danheiser, R. L.; Gould, A. E.; de la Pradilla, R. F.; Helgason, A. L. J. Org. Chem. 1994, 59, 5514.
4. Intramolecular annulation of arene-ynes and alkynes: (d) Lian, J.-J.; Chen, P.-C.; Lin, Y.-P.; Ting, H.-C.; Liu, R.-S. J. Am. Chem. Soc. 2006, 128, 11372.
5. (e) Rodriguez, D.; Martinez-Esperon, M. F.; Navarro-Vazquez, A.; Castedo, L.; Dominguez, D.; Saa, C. J. Org. Chem. 2004, 69, 3842.
6. (a) Agenet, N.; Gandon, V.; Vollhardt, K. P. C.; Malacria, M.; Aubert, C. J. Am. Chem. Soc. 2007, 129, 8860.
7. For a review, see: (b) Chopade, P. R.; Louie, J. Adv. Synth. Catal. 2006, 348, 2307.
8. (a) Rubina, M.; Conley, M.; Gevorgyan, V. J. Am. Chem. Soc. 2006, 128, 5818.
9. (b) Saito, S.; Salter, M. M.; Gevorgyan, V.; Tsuboya, N.; Tando, K.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 3970.
10. For a review, see: (c) Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232.
11. Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117.
12. Cyclopropanations of enynes are surprisingly undeveloped. (a) Gmyzina, R. N.; D'yakonov, I. A.; Danilkina, L. P. Zhur. Obshch. Khimii 1970, 6, 2168.
13. (b) Shapiro, E. A.; Romanova, T. N.; Dolgii, I. E.; Nefedov, O. M. Izv. Akadem. Nauk SSSR, Seriya Khimicheskaya 1985, 11, 2535.
14. (c) Kretschik, O.; Nieger, M.; Dotz, K. H. Chem. Ber. 1995, 128, 987.
15. (d) Du, H.; Long, J.; Shi, Y. Org. Lett. 2006, 8, 2827.
16. (a) Gorin, D. J.; Dube, P.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 14480.
17. (b) Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 18002.
18. (c) Shi, X.; Gorin, D. J.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 5802.
19. See also: (d) Lopez, S.; Herrero-Gomez, E.; Perez-Galan, P.; Nieto-Oberhuber, C; Echavarren, A. M. Angew. Chem. Int. Ed. 2006, 45, 6029.
20. (a) Miki, K.; Ohe, K.; Uemura, S. Tetrahedron Lett. 2003, 44, 2019.
21. (b) Miki, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2003, 68, 8505.
22. (c) Ikeda, Y.; Murai, M.; Abo, T.; Miki, K.; Ohe, K. Tetrahedron Lett. 2007, 48, 6651.
23. For recent reviews of gold-catalyzed reactions, see: (a) Jimenez-Nunez, E.; Echavarren, A. M. Chem. Commun. 2007, 333.
24. (b) Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395.
25. (c) Furstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410.
26. (a) Neher, D. Macromol. Rapid Commun. 2001, 22, 1365.
27. (b) Scherf, U.; List, E. Adv. Mater. 2002, 14, 477.
28. (c) Leclerc, M. J. Polym Sci., Part A: Polym. Chem. 2001, 39, 2867.
29. The synthesis of substituted fluorenes is generally accomplished by [9,9]-dialkylation of fluorene followed by [2,7]-dibromination and subsequent functionalization. See, for example: Tsuie, B.; Reddinger, J. L.; Sotzing, G. A.; Soloducho, J.; Katritzky, A. R.; Reynolds, J. R. J. Mater. Chem. 1999, 9, 2189.
30. For [3,3] rearrangements of cis-vinyl-alkynyl-cyclopropanes, see: metal-mediated: (a) Ohe, K.; Yokoi, T.; Miki, K.; Nishino, F.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 526.
31. Thermal: (b) Dolbier, W. R., Jr.; Garza, O. T.; Al-Sader, B. H. J. Am. Chem. Soc. 1975, 97, 5038.
32. For Au-catalyzed benzannulations, see: (a) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553.
33. (b) Dankwardt, J. W. Tetrahedron Lett. 2001, 42, 5809.
34. (c) Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650.
35. (d) Asao, N. Synlett 2006, 11, 1645.
36. (e) Zhao, J.; Hughes, C. O.; Toste, F. D. J. Am. Chem. Soc. 2006, 125, 7436. Also see refs 1d , 6a.
37. 6 resulted in 63% 4 and 34% 3.
38. Optimization of the one-pot synthesis produced 4 in lower yield from 1 and 2. See Supporting Information.
39. 89 was isolated and resubjected to the reaction conditions with and without the addition of triarylphosphite gold(I) chloride to afford the expected products, suggesting the possibility for silver or acid catalysis in the final step. Control experiments indicate that neither AgOTf nor HOTf catalyze the cycloisomerization of 5. See Supporting Information.
40. Further experiments (see Supporting Information) indicate that 3 readily isomerizes to 4 under strongly acidic conditions. A deuterium-labeling experiment suggested that this is not a major pathway for the formation of 4 under our reaction conditions: (Chemical Equation Presented)