Pd0-catalyzed cyclization reaction of aryl or alk-1-enyl halides with 1,2-dienyl ketones: A general and efficient synthesis of polysubstituted furans

Chemical Communications

Volumn , Issue 2, 2000, Pages 117-118

  Ma, Shengming ^a   Zhang, Junliang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; SYNTHESIS;

EID: 0034695528     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a908627g     Document Type: Article

References (45)

1. F. M. Dean, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katrizky and C. W. Rees, Pergamon, New York, 1984, vol. 4, p. 313; M. U. Sargent, p. 599; D. M. X. Donnelly, p. 651; R. Benassi, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katrizky, C. W. Rees and E. F. U. Scriven, Pergamon, New York, 1996, vol. 2, p. 259; H. Heaney, p. 297; B. A. Keay, p. 395; K. Nakanishi, Natural Products Chemistry, Kodamsha, Tokyo, 1974; M. Shipman, Contemp. Org. Synth., 1995, 2, 1.
2. F. M. Dean, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katrizky and C. W. Rees, Pergamon, New York, 1984, vol. 4, p. 313; M. U. Sargent, p. 599; D. M. X. Donnelly, p. 651; R. Benassi, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katrizky, C. W. Rees and E. F. U. Scriven, Pergamon, New York, 1996, vol. 2, p. 259; H. Heaney, p. 297; B. A. Keay, p. 395; K. Nakanishi, Natural Products Chemistry, Kodamsha, Tokyo, 1974; M. Shipman, Contemp. Org. Synth., 1995, 2, 1.
3. F. M. Dean, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katrizky and C. W. Rees, Pergamon, New York, 1984, vol. 4, p. 313; M. U. Sargent, p. 599; D. M. X. Donnelly, p. 651; R. Benassi, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katrizky, C. W. Rees and E. F. U. Scriven, Pergamon, New York, 1996, vol. 2, p. 259; H. Heaney, p. 297; B. A. Keay, p. 395; K. Nakanishi, Natural Products Chemistry, Kodamsha, Tokyo, 1974; M. Shipman, Contemp. Org. Synth., 1995, 2, 1.
4. F. M. Dean, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katrizky and C. W. Rees, Pergamon, New York, 1984, vol. 4, p. 313; M. U. Sargent, p. 599; D. M. X. Donnelly, p. 651; R. Benassi, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katrizky, C. W. Rees and E. F. U. Scriven, Pergamon, New York, 1996, vol. 2, p. 259; H. Heaney, p. 297; B. A. Keay, p. 395; K. Nakanishi, Natural Products Chemistry, Kodamsha, Tokyo, 1974; M. Shipman, Contemp. Org. Synth., 1995, 2, 1.
5. F. M. Dean, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katrizky and C. W. Rees, Pergamon, New York, 1984, vol. 4, p. 313; M. U. Sargent, p. 599; D. M. X. Donnelly, p. 651; R. Benassi, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katrizky, C. W. Rees and E. F. U. Scriven, Pergamon, New York, 1996, vol. 2, p. 259; H. Heaney, p. 297; B. A. Keay, p. 395; K. Nakanishi, Natural Products Chemistry, Kodamsha, Tokyo, 1974; M. Shipman, Contemp. Org. Synth., 1995, 2, 1.
6. F. M. Dean, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katrizky and C. W. Rees, Pergamon, New York, 1984, vol. 4, p. 313; M. U. Sargent, p. 599; D. M. X. Donnelly, p. 651; R. Benassi, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katrizky, C. W. Rees and E. F. U. Scriven, Pergamon, New York, 1996, vol. 2, p. 259; H. Heaney, p. 297; B. A. Keay, p. 395; K. Nakanishi, Natural Products Chemistry, Kodamsha, Tokyo, 1974; M. Shipman, Contemp. Org. Synth., 1995, 2, 1.
7. F. M. Dean, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katrizky and C. W. Rees, Pergamon, New York, 1984, vol. 4, p. 313; M. U. Sargent, p. 599; D. M. X. Donnelly, p. 651; R. Benassi, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katrizky, C. W. Rees and E. F. U. Scriven, Pergamon, New York, 1996, vol. 2, p. 259; H. Heaney, p. 297; B. A. Keay, p. 395; K. Nakanishi, Natural Products Chemistry, Kodamsha, Tokyo, 1974; M. Shipman, Contemp. Org. Synth., 1995, 2, 1.
8. F. M. Dean, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katrizky and C. W. Rees, Pergamon, New York, 1984, vol. 4, p. 313; M. U. Sargent, p. 599; D. M. X. Donnelly, p. 651; R. Benassi, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katrizky, C. W. Rees and E. F. U. Scriven, Pergamon, New York, 1996, vol. 2, p. 259; H. Heaney, p. 297; B. A. Keay, p. 395; K. Nakanishi, Natural Products Chemistry, Kodamsha, Tokyo, 1974; M. Shipman, Contemp. Org. Synth., 1995, 2, 1.
9. Common Fragrance and Flavor Materials, ed. K. Bauer and D. Garbe, VCH, Weinheim, 1985.
10. B. H. Lipshutz, Chem. Rev., 1986, 86, 795.
11. For most recent reviews, see: X. Hou, H. Y. Cheung, T. Y. Hon, P. L. Kwan, T. H. Lo, S. Y. Tong and H. N. C. Wong, Tetrahedron, 1998, 54, 1955; B. A. Keay, Chem. Soc. Rev., 1999, 28, 209.
12. For most recent reviews, see: X. Hou, H. Y. Cheung, T. Y. Hon, P. L. Kwan, T. H. Lo, S. Y. Tong and H. N. C. Wong, Tetrahedron, 1998, 54, 1955; B. A. Keay, Chem. Soc. Rev., 1999, 28, 209.
13. E. Bures, J. A. Nieman, S. Yu, P. G. Spinazzé, J. J. Bontront, I. R. Hunt, A. Rauk and B. A. Keay, J. Org. Chem., 1997, 62, 8750; E. Bures, P. G. Spinazz, G. Beese, I. R. Hunt, C. Rogers and B. A. Keay, J. Org. Chem., 1997, 62, 8741; T. Bach and L. Krüger, Tetrahedron Lett., 1998, 39, 1729.
14. E. Bures, J. A. Nieman, S. Yu, P. G. Spinazzé, J. J. Bontront, I. R. Hunt, A. Rauk and B. A. Keay, J. Org. Chem., 1997, 62, 8750; E. Bures, P. G. Spinazz, G. Beese, I. R. Hunt, C. Rogers and B. A. Keay, J. Org. Chem., 1997, 62, 8741; T. Bach and L. Krüger, Tetrahedron Lett., 1998, 39, 1729.
15. E. Bures, J. A. Nieman, S. Yu, P. G. Spinazzé, J. J. Bontront, I. R. Hunt, A. Rauk and B. A. Keay, J. Org. Chem., 1997, 62, 8750; E. Bures, P. G. Spinazz, G. Beese, I. R. Hunt, C. Rogers and B. A. Keay, J. Org. Chem., 1997, 62, 8741; T. Bach and L. Krüger, Tetrahedron Lett., 1998, 39, 1729.
16. I. Heilbron, E. R. H. Jones and F. Sondheimer, J. Chem. Soc., 1947, 1586; T. L. Jacobs, D. Dankner and A. R. Dankner, J. Am. Chem. Soc., 1958, 80, 864; S. R. Landor and E. S. Pepper, J. Chem. Soc. (C), 1966, 2283; G. Büchi and H. Wüest, J. Org. Chem., 1969, 34, 857; B. Gabriele, G. Salerno, F. De Pascali, G. T. Sciano, M. Costa and G. P. Chiusoli, Tetrahedron Lett., 1997, 38, 6877; S. Cacchi, G. Fabrizi and L. Moro, J. Org. Chem., 1997, 62, 5327; A. Arcadi and E. Rossi, Tetrahedron, 1998, 54, 15253; D. I. MaGee, J. D. Leach and S. Setiadji, Tetrahedron, 1999, 55, 2847.
17. I. Heilbron, E. R. H. Jones and F. Sondheimer, J. Chem. Soc., 1947, 1586; T. L. Jacobs, D. Dankner and A. R. Dankner, J. Am. Chem. Soc., 1958, 80, 864; S. R. Landor and E. S. Pepper, J. Chem. Soc. (C), 1966, 2283; G. Büchi and H. Wüest, J. Org. Chem., 1969, 34, 857; B. Gabriele, G. Salerno, F. De Pascali, G. T. Sciano, M. Costa and G. P. Chiusoli, Tetrahedron Lett., 1997, 38, 6877; S. Cacchi, G. Fabrizi and L. Moro, J. Org. Chem., 1997, 62, 5327; A. Arcadi and E. Rossi, Tetrahedron, 1998, 54, 15253; D. I. MaGee, J. D. Leach and S. Setiadji, Tetrahedron, 1999, 55, 2847.
18. I. Heilbron, E. R. H. Jones and F. Sondheimer, J. Chem. Soc., 1947, 1586; T. L. Jacobs, D. Dankner and A. R. Dankner, J. Am. Chem. Soc., 1958, 80, 864; S. R. Landor and E. S. Pepper, J. Chem. Soc. (C), 1966, 2283; G. Büchi and H. Wüest, J. Org. Chem., 1969, 34, 857; B. Gabriele, G. Salerno, F. De Pascali, G. T. Sciano, M. Costa and G. P. Chiusoli, Tetrahedron Lett., 1997, 38, 6877; S. Cacchi, G. Fabrizi and L. Moro, J. Org. Chem., 1997, 62, 5327; A. Arcadi and E. Rossi, Tetrahedron, 1998, 54, 15253; D. I. MaGee, J. D. Leach and S. Setiadji, Tetrahedron, 1999, 55, 2847.
19. I. Heilbron, E. R. H. Jones and F. Sondheimer, J. Chem. Soc., 1947, 1586; T. L. Jacobs, D. Dankner and A. R. Dankner, J. Am. Chem. Soc., 1958, 80, 864; S. R. Landor and E. S. Pepper, J. Chem. Soc. (C), 1966, 2283; G. Büchi and H. Wüest, J. Org. Chem., 1969, 34, 857; B. Gabriele, G. Salerno, F. De Pascali, G. T. Sciano, M. Costa and G. P. Chiusoli, Tetrahedron Lett., 1997, 38, 6877; S. Cacchi, G. Fabrizi and L. Moro, J. Org. Chem., 1997, 62, 5327; A. Arcadi and E. Rossi, Tetrahedron, 1998, 54, 15253; D. I. MaGee, J. D. Leach and S. Setiadji, Tetrahedron, 1999, 55, 2847.
20. I. Heilbron, E. R. H. Jones and F. Sondheimer, J. Chem. Soc., 1947, 1586; T. L. Jacobs, D. Dankner and A. R. Dankner, J. Am. Chem. Soc., 1958, 80, 864; S. R. Landor and E. S. Pepper, J. Chem. Soc. (C), 1966, 2283; G. Büchi and H. Wüest, J. Org. Chem., 1969, 34, 857; B. Gabriele, G. Salerno, F. De Pascali, G. T. Sciano, M. Costa and G. P. Chiusoli, Tetrahedron Lett., 1997, 38, 6877; S. Cacchi, G. Fabrizi and L. Moro, J. Org. Chem., 1997, 62, 5327; A. Arcadi and E. Rossi, Tetrahedron, 1998, 54, 15253; D. I. MaGee, J. D. Leach and S. Setiadji, Tetrahedron, 1999, 55, 2847.
21. I. Heilbron, E. R. H. Jones and F. Sondheimer, J. Chem. Soc., 1947, 1586; T. L. Jacobs, D. Dankner and A. R. Dankner, J. Am. Chem. Soc., 1958, 80, 864; S. R. Landor and E. S. Pepper, J. Chem. Soc. (C), 1966, 2283; G. Büchi and H. Wüest, J. Org. Chem., 1969, 34, 857; B. Gabriele, G. Salerno, F. De Pascali, G. T. Sciano, M. Costa and G. P. Chiusoli, Tetrahedron Lett., 1997, 38, 6877; S. Cacchi, G. Fabrizi and L. Moro, J. Org. Chem., 1997, 62, 5327; A. Arcadi and E. Rossi, Tetrahedron, 1998, 54, 15253; D. I. MaGee, J. D. Leach and S. Setiadji, Tetrahedron, 1999, 55, 2847.
22. I. Heilbron, E. R. H. Jones and F. Sondheimer, J. Chem. Soc., 1947, 1586; T. L. Jacobs, D. Dankner and A. R. Dankner, J. Am. Chem. Soc., 1958, 80, 864; S. R. Landor and E. S. Pepper, J. Chem. Soc. (C), 1966, 2283; G. Büchi and H. Wüest, J. Org. Chem., 1969, 34, 857; B. Gabriele, G. Salerno, F. De Pascali, G. T. Sciano, M. Costa and G. P. Chiusoli, Tetrahedron Lett., 1997, 38, 6877; S. Cacchi, G. Fabrizi and L. Moro, J. Org. Chem., 1997, 62, 5327; A. Arcadi and E. Rossi, Tetrahedron, 1998, 54, 15253; D. I. MaGee, J. D. Leach and S. Setiadji, Tetrahedron, 1999, 55, 2847.
23. I. Heilbron, E. R. H. Jones and F. Sondheimer, J. Chem. Soc., 1947, 1586; T. L. Jacobs, D. Dankner and A. R. Dankner, J. Am. Chem. Soc., 1958, 80, 864; S. R. Landor and E. S. Pepper, J. Chem. Soc. (C), 1966, 2283; G. Büchi and H. Wüest, J. Org. Chem., 1969, 34, 857; B. Gabriele, G. Salerno, F. De Pascali, G. T. Sciano, M. Costa and G. P. Chiusoli, Tetrahedron Lett., 1997, 38, 6877; S. Cacchi, G. Fabrizi and L. Moro, J. Org. Chem., 1997, 62, 5327; A. Arcadi and E. Rossi, Tetrahedron, 1998, 54, 15253; D. I. MaGee, J. D. Leach and S. Setiadji, Tetrahedron, 1999, 55, 2847.
24. I. M. Heilbron, E. R. H. Jones, P. Smith and B. C. L. Weedon, J. Chem. Soc., 1946, 54; D. Miller, J. Chem. Soc. (C), 1969, 12; Y. Wakabayashi, Y. Fukuda, H. Shiragami, K. Utimoto and H. Nozaki, Tetrahedron, 1985, 41, 3655; Y. Fukuda, H. Shiragami, K. Utimoto and H. Nozaki, J. Org. Chem., 1991, 56, 5816.
25. I. M. Heilbron, E. R. H. Jones, P. Smith and B. C. L. Weedon, J. Chem. Soc., 1946, 54; D. Miller, J. Chem. Soc. (C), 1969, 12; Y. Wakabayashi, Y. Fukuda, H. Shiragami, K. Utimoto and H. Nozaki, Tetrahedron, 1985, 41, 3655; Y. Fukuda, H. Shiragami, K. Utimoto and H. Nozaki, J. Org. Chem., 1991, 56, 5816.
26. I. M. Heilbron, E. R. H. Jones, P. Smith and B. C. L. Weedon, J. Chem. Soc., 1946, 54; D. Miller, J. Chem. Soc. (C), 1969, 12; Y. Wakabayashi, Y. Fukuda, H. Shiragami, K. Utimoto and H. Nozaki, Tetrahedron, 1985, 41, 3655; Y. Fukuda, H. Shiragami, K. Utimoto and H. Nozaki, J. Org. Chem., 1991, 56, 5816.
27. I. M. Heilbron, E. R. H. Jones, P. Smith and B. C. L. Weedon, J. Chem. Soc., 1946, 54; D. Miller, J. Chem. Soc. (C), 1969, 12; Y. Wakabayashi, Y. Fukuda, H. Shiragami, K. Utimoto and H. Nozaki, Tetrahedron, 1985, 41, 3655; Y. Fukuda, H. Shiragami, K. Utimoto and H. Nozaki, J. Org. Chem., 1991, 56, 5816.
28. R. L. Danheiser, E. J. Stoner, H. Koyama, D. S. Yamashita and C. A. Klade, J. Am. Chem. Soc., 1989, 111, 4407.
29. C. M. Marson and S. Harper, J. Org. Chem., 1998, 63, 9223.
30. F.-T. Lou, A. C. Bajji and A. Jeevanandam, J. Org. Chem., 1999, 64, 1738; F.-T. Lou, A. Jeevanandam and A. C. Bajji, Tetrahedron Lett., 1999, 40, 121.
31. F.-T. Lou, A. C. Bajji and A. Jeevanandam, J. Org. Chem., 1999, 64, 1738; F.-T. Lou, A. Jeevanandam and A. C. Bajji, Tetrahedron Lett., 1999, 40, 121.
32. J. A. Marshall and E. D. Robinson, J. Org. Chem., 1990, 55, 3450; J. A. Marshall and X. Wang, J. Org. Chem., 1991, 56, 960; J. A. Marshall and E. M. Wallace, J. Org. Chem., 1995, 60, 796.
33. J. A. Marshall and E. D. Robinson, J. Org. Chem., 1990, 55, 3450; J. A. Marshall and X. Wang, J. Org. Chem., 1991, 56, 960; J. A. Marshall and E. M. Wallace, J. Org. Chem., 1995, 60, 796.
34. J. A. Marshall and E. D. Robinson, J. Org. Chem., 1990, 55, 3450; J. A. Marshall and X. Wang, J. Org. Chem., 1991, 56, 960; J. A. Marshall and E. M. Wallace, J. Org. Chem., 1995, 60, 796.
35. For the hydrohalogenation reaction of electron-deficient allenes, see: (a) S. Ma, Z. Shi and L. Li, J. Org. Chem., 1998, 63, 4522;
36. (b) S. Ma and Q. Wei, J. Org. Chem., 1999, 64, 1028;
37. S. Ma and L. Li, H. Xie, J. Org. Chem., 1999, 64, 5325.
38. +-cocatalyzed cyclization of organic halides with 1,2-allenyl carboxylic acids to afford β-butenolides, see: S. Ma and Z. Shi, J. Org. Chem., 1998, 63, 6387; For the corresponding reaction with 2,3-dienols with organic halides to afford oxiranes, see: S. Ma and S. Zhao, J. Am. Chem. Soc., 1999, 121, 7943.
39. +-cocatalyzed cyclization of organic halides with 1,2-allenyl carboxylic acids to afford β-butenolides, see: S. Ma and Z. Shi, J. Org. Chem., 1998, 63, 6387; For the corresponding reaction with 2,3-dienols with organic halides to afford oxiranes, see: S. Ma and S. Zhao, J. Am. Chem. Soc., 1999, 121, 7943.
40. II-catalyzed direct cyclization and dimerization of terminal allenyl ketones to afford a mixture of 2-monosubstituted furans and 2,4-disubstituted furans, see: (a) A. S. K. Hashmi, Angew. Chem., 1995, 107, 1749; Angew. Chem., Int. Ed. Engl., 1995, 34, 1581;
41. II-catalyzed direct cyclization and dimerization of terminal allenyl ketones to afford a mixture of 2-monosubstituted furans and 2,4-disubstituted furans, see: (a) A. S. K. Hashmi, Angew. Chem., 1995, 107, 1749; Angew. Chem., Int. Ed. Engl., 1995, 34, 1581;
42. (b) A. S. K. Hashmi, T. L. Ruppert, T. Knofel and J. W. Bats, J. Org. Chem., 1997, 62, 7295. In most cases, the dimerization products are predominant.
43. N. A. Petasis and K. A. Teets, J. Am. Chem. Soc., 1992, 114, 10328.
44. S. Ma, X. Lu and Z. Li, J. Org. Chem., 1992, 57, 709. For a review, see: X. Lu and S. Ma, Chin. J. Chem., 1998, 16, 388.
45. S. Ma, X. Lu and Z. Li, J. Org. Chem., 1992, 57, 709. For a review, see: X. Lu and S. Ma, Chin. J. Chem., 1998, 16, 388.