Synthesis of highly substituted furans by the electrophile-induced coupling of 2-(1-alkynyl)-2-alken-1-ones and nucleophiles

Journal of Organic Chemistry

Volumn 70, Issue 19, 2005, Pages 7679-7685

  Yao, Tuanli ^a   Zhang, Xiaoxia ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CARBOXYLIC ACIDS; CATALYSIS; CATALYSTS; KETONES; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ARENES; COUPLING; FURANS; NUCLEOPHILES;

FURAN RESINS;

1,3 DIKETONE; ALKYNE; CARBOXYLIC ACID; FURAN DERIVATIVE; GOLD CHLORIDE; IODINE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CATALYSIS; CHEMICAL BOND; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

FURANS; ISOMERISM;

EID: 24944453027     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0510585     Document Type: Article

References (73)

1. (a) Dean, F. A. Naturally Occurring Oxygen Ring Compounds; Butterworth: London, UK, 1963.
2. (b) Natural Products Chemistry; Nakanishi, K., Goto, T., Ito, S., Natori, S., Nozoe, S., Eds.; Kodansha, Ltd.: Tokyo, Japan, 1974; Vois. 1-3.
3. (c) Dean, F. M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: New York, 1982; Vol. 30, pp 167-238.
4. (d) Dean, F. M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: New York, 1983; Vol. 31, pp 237-344.
5. (e) Sargent, M. V.; Dean, F. M. In Comprehensive Heterocyclic Chemistry; Bird, C. W., Cheeseman, G. W. H., Eds.; Pergamon Press: Oxford, UK, 1984; Vol. 3, pp 599-656.
6. (f) Lipshutz, B. H. Chem. Rev. 1986, 86, 795-819.
7. (a) Lee, J.; Li, J.-H.; Oya, S.; Snyder, J. K. J. Org. Chem. 1992, 57, 5301-5312.
8. (b) Padwa, A.; Ishida, M.; Muller, C. L.; Murphree, S. S. J. Org. Chem. 1992, 57, 1170-1178.
9. (c) Jacobi, P. A.; Selnick, H. G. J. Org. Chem. 1990, 55, 202-209.
10. (a) Benesova, V.; Samek, Z.; Herout, V.; Sorm, F. Collect. Czech. Chem. Commun. 1969, 34, 1807-1809.
11. (b) Corbella, A.; Gariboldi, P.; Jommi, G.; Orsini, F.; De Marco, A.; Immirzi, A. J. Chem. Soc., Perkin Trans. 1 1974, 1875-1878.
12. (a) Kazlauskas, R.; Murphy, P. T.; Wells, R. J.; Daly, J. J.; Schoenholzer, P. Tetrahedron Lett. 1978, 19, 4951-4954.
13. (b) Richou, O.; Vaillancourt, V.; Faulkner, D. J.; Albizati, K. F. J. Org. Chem. 1989, 54, 4729-4730.
14. (a) King, F. E.; King, T. J.; Neill, K. G. J. Chem. Soc. 1953, 1055-1059.
15. (b) King, F. E.; King, T. J. J. Chem. Soc. 1953, 4158-4168.
16. (c) King, F. E.; Godson, D. H.; King, T. J. J. Chem. Soc. 1955, 1117-1125.
17. (a) Nakanishi, K. Natural Products Chemistry; Kodansha, Ltd.: Tokyo, Japan, 1974.
18. (b) The Chemistry of Heterocyclic Flavoring and Aroma Compounds; Vernin, G., Ed.; Ellis Horwood: Chichester, UK, 1982.
19. (c) Kubo, I.; Lee, Y. W.; Balogh-Nair, V.; Nakanishi, K.; Chapya, A. J. Chem. Soc., Chem. Commun. 1976, 949-950.
20. (d) Schulte, G.; Scheuer, P. J.; McConnell, O. J. Helv. Chim. Acta 1980, 63, 2159-2167.
21. (a) Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; J. Wiley: New York, 1989.
22. (b) Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis; VCH: Weinheim, Germany, 1996.
23. (a) Benassi, R. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, UK, 1996; Vol. 2, pp 259-295.
24. (b) Heaney, H.; Ahn, J. S. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, UK, 1996; Vol. 2, pp 297-357.
25. (c) Friedrichsen, W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, UK, 1996; Vol. 2, pp 351-393.
26. (d) Keay, B. A.; Dibble, P. W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, UK, 1996; Vol. 2, pp 395-436.
27. (e) Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991.
28. Recent reviews: (a) Hou, X. L.; Yang, Z.; Wong, H. N. C. In Progress in Heterocyclic Chemistry; Gribble, G. W., Gilchrist, T. L., Eds.; Pergamon Press: Oxford, UK, 2002; Vol. 14, pp 139-179.
29. (b) Cacchi, S. J. Organomet. Chem. 1999, 576, 42-64.
30. (c) Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C. Tetrahedron 1998, 54, 1955-2020.
31. (a) Sheng, H.; Lin, S.; Huang, Y. Tetrahedron Lett. 1986, 27, 4893-4894.
32. (b) Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1991, 56, 5816-5819.
33. (c) Kel'in, A. V.; Gevorgyan, V. J. Org. Chem. 2002, 67, 95-98.
34. (d) Ma, S.; Zhang, J. Chem. Commun. 2000, 117-118.
35. (e) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1992, 57, 3387-3396.
36. (f) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 960-969.
37. (g) Marshall, J. A.; Bartley, G. S. J. Org. Chem. 1994, 59, 7169-7171.
38. (h) Arcadi, A.; Cacchi, S.; Larock, R. C.; Marinelli, F. Tetrahedron Lett. 1993, 34, 2813-2816.
39. (i) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285-2288.
40. (a) Wakabayashi, Y.; Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. Tetrahedron 1985, 41, 3655-3661.
41. (b) Gabriele, B.; Salerno, G.; Lauria, E. J. Org. Chem. 1999, 64, 7687-7692.
42. (c) Seiller, B.; Bruneau, C.; Dixneuf, P. H. J. Chem. Soc., Chem. Commun. 1994, 493-494.
43. (d) Seiller, B.; Bruneau, C.; Dixneuf, P. H. Tetrahedron 1995, 51, 13089-13102.
44. (e) Kücükbay, H.; Cetinkaya, B.; Guesmi, S.; Dixneuf, P. H. Organometallics 1996, 15, 2434-2439.
45. (a) Lo, C.-Y.; Guo, H.; Lian, J.-J.; Shen, F.-M.; Liu, R.-S. J. Org. Chem. 2002, 67, 3930-3932.
46. (b) Marshall, J. A.; DuBay, W. J. J. Am. Chem. Soc. 1992, 114, 1450-1456.
47. (c) Hashmi, A. S. K.; Sinha, P. Adv. Synth. Catal. 2004, 346, 432-438.
48. Bew, S. P.; Knight, D. W. Chem. Commun. 1996, 1007-1008.
49. Stefani, H. A.; Petragnani, N.; Valduga, C. J.; Brandt, C. A. Tetrahedron Lett. 1997, 38, 4977-4980.
50. (a) Rao, M. S.; Esho, N.; Sergeant, C.; Dembinski, R. J. Org. Chem. 2003, 68, 6788-6790.
51. (b) Sniady, A.; Wheeler, K. A.; Dembinski, R. Org. Lett. 2005, 7, 1769-1772.
52. Miller, M. W.; Johnson, C. R. J. Org. Chem. 1997, 62, 1582-1583.
53. (a) Yao, T.; Zhang, X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164-11165.
54. (b) For a review of gold catalysis, see: Hashmi, A. S. K. Gold Bull. 2004, 37, 51-65.
55. (c) For the same reaction catalyzed by copper(I), see: Patll, N. T.; Wu, H.; Yamamoto, Y. J. Org. Chem. 2005, 70, 4531-4534.
56. Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 9578-9579 and references therein.
57. (a) Teles, J. H.; Brod, S.; Chabanas, M. Angew. Chem., Int. Ed. 1998, 37, 1415-1418.
58. (b) Mizushima, E.; Sato, K.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563-4565.
59. (c) Casado, R.; Contel, M.; Laguna, M.; Romero, P.; Sanz, S. J. Am. Chem. Soc. 2003, 125, 11925-11935.
60. (d) Fukuda, Y.; Utimoto, K. J. Org. Chem. 1991, 56, 3729-3731.
61. (e) Hoffmann-Roder, A.; Krause, N. Org. Lett. 2001, 3, 2537-2538.
62. Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894-7895.
63. For the dehalogenation of halofurans, see: Gronowitz, S.; Holm, B. J. Heterocycl. Chem. 1977, 14, 281-288.
64. We gratefully acknowledge a reviewer, who recommended this experiment.
65. Abbiati, G.; Arcadi, A.; Bianchi, G.; Di Giuseppe, S.; Marinelli, F.; Rossi, E. E. J. Org. Chem. 2003, 68, 6959-6966.
66. Kobayashi, S.; Kakumoto, K.; Sugiura, M. Org. Lett. 2002, 4, 1319-1322.
67. (a) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2-3.
68. (b) Hughes, C. C.; Trauner, D. Angew. Chem., Int. Ed. 2002, 41, 1569-1572.
69. Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479-11502.
70. Knight, S. D.; Overman, L. E. Heterocycles 1994, 39, 497-501.
71. (a) Konaklieva, M. I.; Shi, H.; Turos, E. Tetrahedron Lett. 1997, 38, 8647-8650.
72. (b) Campo, M. A.; Larock, R. C. J. Org. Chem. 2002, 67, 5616-5620.
73. Zambias, R. A.; Caldwell, C. G.; Kopka, I. E.; Hammond, M. L. J. Org. Chem. 1988, 53, 4135-4137.