The Au(I)-catalyzed intramolecular hydroarylation of terminal alkynes under mild conditions: Application to the synthesis of 2H-chromenes, coumarins, benzofurans, and dihydroquinolines

Journal of Organic Chemistry

Volumn 74, Issue 22, 2009, Pages 8901-8903

  Menon, Rajeev S ^a   Findlay, Alison D ^a   Bissember, Alex C ^a   Banwell, Martin G ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURANS; CATALYST LOADINGS; CHEMICAL EQUATIONS; CHROMENES; CO CATALYSTS; HIGH YIELD; HYDROARYLATION; MILD REACTION; SHORT REACTION TIME; STARTING MATERIALS; TERMINAL ALKYNE;

SYNTHESIS (CHEMICAL);

ACETYLENE;

ALKYNE; BENZOFURAN DERIVATIVE; CARBON; CHROMENE DERIVATIVE; COUMARIN DERIVATIVE; DIHYDROQUINOLINE DERIVATIVE; GOLD COMPLEX; HETEROCYCLIC COMPOUND; METAL COMPLEX;

ARTICLE; ARYLATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE;

ALKYNES; BENZOFURANS; BENZOPYRANS; CATALYSIS; COUMARINS; GOLD; MOLECULAR STRUCTURE; QUINOLINES; STEREOISOMERISM;

EID: 70449659209     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902032p     Document Type: Article

References (50)

1. Recent reviews: (a) Hashmi, A. S. K.; Hutchings, G. J. Angew. Chem., Int. Ed. 2006, 45, 7896.
2. (b) Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410.
3. (c) Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395.
4. (d) Hashmi, A. S. K. Nature 2007, 449, 292.
5. (e) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.
6. (f) Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239.
7. (g) Jiménez-Núñez, E.; Echavarren, A.M. Chem. Rev. 2008, 108, 3326.
8. (h) Arcadi, A. Chem. Rev. 2008, 108, 3266.
9. (i) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351.
10. (a) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526.
11. (b) Luzung, M. R.; Markham, J. P.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 10858.
12. (c) Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 18002.
13. (d) Nieto-Oberhuber, C.; López, S.; Echavarren, A. M. J. Am. Chem. Soc. 2005, 127, 6178.
14. (e)Mézailles, N.; Ricard, L.; Gagosz, F. Org. Lett. 2005, 7, 4133.
15. (f) Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271.
16. (g) Nieto-Oberhuber, C.; Pérez-Galán, P.; Herrero-Gómez, E.; Lauterbach, T.; Rodrŕguez, C.; López, S.;Bour, C.;Rosellón, A.;Cárdenas,D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2008, 130, 269.
17. (a) Nevado, C.; Echavarren, A. M. Chem. Eur. J. 2005, 11, 3155.
18. (b) Curtis, N. R.; Prodger, J. C.; Rassias, G.; Walker, A. J. Tetrahedron Lett. 2008, 49, 6279.
19. Herrero-Gómez, E.; Nieto-Oberhuber, C.; López, S.; Benet-Buchholz, J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2006, 45, 5455.
20. (a) Jiménez-Núñez, E.; Claverie, C. K.; Nieto-Oberhuber, C.;Echavarren, A. M. Angew. Chem., Int. Ed. 2006, 45, 5452.
21. (b) Ferrer, C.; Echavarren, A. M. Angew. Chem., Int. Ed. 2006, 45, 1105.
22. Banwell, M. G.; Sharp. P. P. Unpublished results.
23. Reviews: (a) Nevado, C.; Echavarren, A. M. Synthesis 2005, 167.
24. (b) Shen,H.C. Tetrahedron 2008, 64, 3885.
25. (c) Skouta, R.;Li,C.-J. Tetrahedron 2008, 64, 4917.
26. (d) Kitamura, T. Eur. J. Org. Chem. 2009, 1111.
27. For examples of the Au(I)-catalyzed IMHA reactions, see: (e) Reetz, M.; Sommer, K. Eur. J. Org. Chem. 2003, 3485.
28. (f) Shi, Z.; He, C. J. Org. Chem. 2004, 69, 3669.
29. (a) Jia, C.; Lu, W.; Oyamada, J.; Kitamura, T.; Matsuda, K.; Irie, M.; Fujiwara, Y. J. Am. Chem. Soc. 2000, 122, 7252.
30. (b) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
31. Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913.
32. (a) Inoue, H.; Chatani, N.; Muari, S. J. Org. Chem. 2002, 67, 1414.
33. (b) Yadav, J. S.; Reddy, B. V. S.; Padmavani, B.; Gupta, M. K. Tetrahedron Lett. 2004, 45, 7577.
34. (a) Fürstner, A.; Mamane, V. J. Org. Chem. 2002, 67, 6264.
35. (b) Fürstner, A.; Mamane, V. Chem. Commun. 2003, 2112.
36. (c) Mamane, V.; Hannen, P.; Fürstner, A. Chem. Eur. J. 2004, 10, 4556.
37. (d) Pastine, S, J.; Youn, S. W.; Sames, D. Org. Lett. 2003, 5, 1055.
38. (e) Pastine, S, J.; Youn, S. W.; Sames, D. Tetrahedron 2003, 59, 8859.
39. Nishizawa, M.; Takao, H.; Yadav, V. K.; Imagawa, H.; Sugihara, T. Org. Lett. 2003, 5, 4563.
40. Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2004, 126, 10204.
41. See the Supporting Information for experimental details.
42. (a) Ishii, H.; Ishikawa, T.; Takeda, S.; Ueki, S.; Suzuki, M. Chem. Pharm. Bull. 1992, 40, 1148.
43. (b) Ishikawa, T.; Nagai, K.; Ohkubo, N.; Ishii, H. Heterocycles 1994, 39, 371.
44. We thank a referee for useful suggestions regarding the reaction pathway proposed in Scheme 2.
45. Robles-Machín, R.; Adrio, J.; Carretero, J. C. J. Org. Chem. 2006, 71, 5023.
46. (a) Fukuyama, T.; Cheung, M.; Jow, C.-K.; Hidai, Y.; Kan, T. Tetrahedron Lett. 1997, 38, 5831.
47. (b) Kurosawa, W.; Kan, T.; Fukuyama, T. Org. Synth. 2002, 79, 186.
48. Pal, M.; Parasuraman, K.; Yeleswarapu, K. R. Org. Lett. 2003, 5, 349.
49. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
50. Varela, J. A.; González-Roríguez, C.; Rubín, S. G.; Castedo, L.; Saá, C. J. Am. Chem. Soc. 2006, 128, 9576.