An efficient and general synthesis of furan-2-acetic esters by palladium-catalyzed oxidative carbonylation of (Z)-2-en-4-yn-1-ols

Journal of Organic Chemistry

Volumn 64, Issue 21, 1999, Pages 7693-7699

  Gabriele, Bartolo ^a   Salerno, Giuseppe ^a   De Pascali, Francesca ^a   Costa, Mirco ^b   Chiusoli, Gian Paolo ^b  

^a UNIVERSITY OF CALABRIA   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2,5 DIHYDROFURAN DERIVATIVE; FURAN 2 ACETIC ESTER; FURAN DERIVATIVE; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CYCLIZATION; ORGANIC CHEMISTRY; OXIDATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032724025     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990848+     Document Type: Article

References (68)

1. (a) Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991.
2. (b) Tsuji, J. Palladium Reagents and Catalysts; Wiley: New York, 1995.
3. A variety of examples of this kind of reactivity have been reported in the literature. Some of most representative, limited to catalysis with palladium, are cited here. (a) Murray, T. F.; Samsel, E. G.; Varma, V.; Norton, J. R. J. Am. Chem. Soc. 1981, 103, 7520-7528.
4. (b) Alper, H.; Leonard, D. J. Chem. Soc., Chem. Commun. 1985, 511-512.
5. (c) Alper, H.; Leonard, D. Tetrahedron Lett. 1985, 26, 5639-5642.
6. (d) Tamaru, Y.; Higashimura, H.; Naka, K.; Hojo, M.; Yoshida, Z. Angew. Chem., Int. Ed. Engl. 1985, 24, 1045-1046.
7. (e) Tamaru, Y.; Hojo, M.; Yoshida, Z.-I. J. Org. Chem. 1991, 56, 1099-1105.
8. (f) El Ali, B.; Alper, H. J. Org. Chem. 1991, 56, 5357-5360.
9. (g) Chenal, T.; Cipres, I.; Jenck, J.; Kalck, P.; Peres, Y. J. Mol. Catal. 1993, 78, 351-366.
10. (h) Gabriele, B.; Costa, M.; Salerno; G.; Chiusoli, G. P. J. Chem. Soc., Chem. Commun. 1994, 1429-1430.
11. (i) Matsushita, K.; Komori, T.; Oi, S.; Inoue, Y. Tetrahedron Lett. 1994, 35, 5889-5890.
12. (j) Ukaji, Y.; Miyamoto, M.; Mikuni, M.; Takeuchi, S.; Inomata, K. Bull. Chem. Soc. Jpn. 1996, 69, 735-742.
13. (k) El Ali, B.; Okuro, K.; Vasapollo, G.; Alper, H. J. Am. Chem. Soc. 1996, 118, 4264-4270.
14. (l) Yu, W.-Y.; Alper, H. J. Org. Chem. 1997, 62, 5684-5687.
15. (m) Gabriele, B.; Salerno, G.; Costa, M.; De Pascali, F.; Chiusoli, G. P. J. Chem. Soc., Perkin Trans. 1 1997, 147-154.
16. (n) Brunner, M.; Alper, H. J. Org. Chem. 1997, 62, 7565-7568.
17. (o) Yu, W.-Y.; Bensimon, C.; Alper, H. Chem. Eur. J. 1997, 3, 417-423.
18. (p) Okuro, K.; Kai, H.; Alper, H. Tetrahedron: Asymmetry 1997, 8, 2307-2309.
19. (q) Tezuka, K.; Ishizaki, Y.; Inoue, Y. J. Mol. Catal. A 1998, 129, 199-206.
20. Some representative examples, limited to catalysis with palladium, are reported here. (a) Hegedus, L. S.; Allen, G. F.; Olsen, D. J. J. Am. Chem. Soc. 1980, 102, 3583-3587.
21. (b) Tamaru, Y.; Yoshida, Z. J. Organomet. Chem. 1987, 334, 213-223 and references therein.
22. (c) Semmelhack, M. F.; Zhang, N. J. Org. Chem. 1989, 54, 4483-4485.
23. (d) McCormick, M.; Monahan, R., III; Soria, J.; Goldsmith, D.; Liotta, D. J. Org. Chem. 1989, 54, 4485-4487.
24. (e) Yadav, J. S.; Rao, E. S.; Rao, C. S.; Choudary, B. M. J. Mol. Catal. 1989, 49, L61-L63.
25. (f) Semmelhack, M. F.; Kim, C.; Zhang, N.; Bodurow, C.; Sanner, M.; Dobler, W.; Meier, M. Pure Appl. Chem. 1990, 62, 2035-2040 and references therein.
26. (g) Kraus, G. A.; Li, J.; Gordon, M. S.; Jensen, J. H. J. Am. Chem. Soc. 1993, 115, 5859.
27. (h) Tamaru, Y.; Kimura, M. Synlett 1997, 749-757 and references therein.
28. (i) Harayama, H.; Abe, A.; Sakado, T.; Kimura, M.; Fugami, K.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1997, 62, 2113-2122.
29. Kondo, Y.; Sakamoto, T.; Yamanaka, H. Heterocycles 1989, 29, 1013-1016.
30. Bonardi, A.; Costa, M.; Gabriele, B.; Salerno G.; Chiusoli, G. P. Tetrahedron Lett. 1995, 36, 7495-7498.
31. Bacchi, A.; Chiusoli, G. P.; Costa, M.; Sani, C.; Gabriele, B.; Salerno, G. J. Organomet. Chem. 1998, 562, 35-43.
32. (a) Bacchi, A.; Chiusoli, G. P., Costa, M., Gabriele, B.; Righi, C.; Salerno, G. Chem. Commun. 1997, 1209-1210.
33. (b) Chiusoli, G. P.; Costa, M.; Gabriele, B.; Salerno, G. J. Mol. Catal. A 1999, 143, 297-310.
34. A preliminary communication of this work was published recently: Gabriele, B.; Salerno, G.; De Pascali, F.; Tomasi Scianò, G.; Costa, M.; Chiusoli, G. P. Tetrahedron Lett. 1997, 38, 6877-6780.
35. See, for example: (a) O'Mant, D. M. Ger. Offen. 1, 919, 381, 1969; Chem. Abstr. 1970, 72, P31599t.
36. See, for example: (a) O'Mant, D. M. Ger. Offen. 1, 919, 381, 1969; Chem. Abstr. 1970, 72, P31599t.
37. (b) Finch, N.; Fitt, J. J.; Hsu, I. H. C. J. Org. Chem. 1971, 36, 3191-3196.
38. (c) Verlaak, J. M. J.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron Lett. 1982, 23, 5463-5466.
39. (d) Kato, S.; Shinichi, K.; Ogasawara, M.; Tetsuo, T. JP 62,205,073, 1987; Chem. Abstr. 1988, 108, P167290e.
40. (d) Kato, S.; Shinichi, K.; Ogasawara, M.; Tetsuo, T. JP 62,205,073, 1987; Chem. Abstr. 1988, 108, P167290e.
41. (e) Cai, J. C.; Shu, H. L.; Tang, C. F.; Komatsu, T.; Matsuno, T.; Narita, T.; Yaguchi, S.; Koide, Y.; Takase, M. Chem. Pharm. Bull. 1989, 37, 2976-2983.
42. (f) Wenkert, E.; Guo, M.; Lavilla, R.; Porter, B.; Ramachandran, K.; Sheu, J.-H. J. Org. Chem. 1990, 55, 6203-6214.
43. (g) Baker, R.; Stevenson, G. I.; Leeson, P. D.; Rowley, M. EP 459,561, 1991; Chem. Abstr. 1992, 116, P151591h.
44. (g) Baker, R.; Stevenson, G. I.; Leeson, P. D.; Rowley, M. EP 459,561, 1991; Chem. Abstr. 1992, 116, P151591h.
45. (h) Shah, S. K.; Dorn, C. P.; Finke, P. E.; Hale, J. J.; Hagmann, W. K.; Brause, K. A.; Chandler, G. O.; Kissinger, A. L.; Ashe, B. M.; Weston, H.; Knight, W. B.; Maycock, A. L.; Dellea, P. S.; Fletcher, D. S.; Hand, K. M.; Mumford, R. A.; Underwood, D. J.; Doherty, J. B. J. Med. Chem. 1992, 35, 3745-3754.
46. (i) Marshall, J. A.; DuBay, W. J. Org. Chem. 1993, 58, 3602-3603.
47. (j) Veverka, M. Il Farmaco 1994, 49, 201-204.
48. (k) Rowley, M.; Kulagowski, J. J.; Watt, A. P.; Rathbone, D.; Stevenson, G. I.; Carling, R. W.; Baker, R.; Marshall, G. R.; Kemp, J. A.; Foster, A. C.; Grimwood, S.; Hargreaves, R.; Hurley, C.; Saywell, K. L.; Tricklebank, M. D.; Leeson, P. D. J. Med. Chem. 1997, 40, 4053-4068.
49. (a) Gabriele, B.; Salerno, G. Chem. Commun. 1997, 1083-1084.
50. (b) Gabriele, B.; Salerno, G.; Lauria, E. J. Org. Chem. 1999, 64, 7687 and references therein.
51. Gabriele, B.; Costa, M.; Salerno, G.; Chiusoli, G. P. J. Chem. Soc., Perkin Trans. 1 1994, 83-87.
52. (a) Alcaide, B.; Casarrubios, L.; Domínguez, G.; Retamosa, A.; Sierra, M. A. Tetrahedron 1996, 52, 13215-13226.
53. (b) Müller, P.; Gränicher, C. Helv. Chim. Acta 1995, 78, 129-144.
54. (c) Nikles, M.; Bur, D.; Séquin, U. Tetrahedron 1990, 46, 1569-1578.
55. (d) Crombie, L.; Crombie, W. M. L. J. Chem. Soc., Perkin Trans. 1 1994, 1267-1274.
56. See, for example, ref 1b and references therein.
57. (a) Murray, T. F.; Varma, V.; Norton, J. R. J. Am. Chem. Soc. 1977, 99, 8085-8087.
58. (b) Murray, T. F.; Norton, J. R. J. Am. Chem. Soc. 1979, 101, 4107-4119.
59. (c) Calderazzo, F. Angew. Chem., Int. Ed. Engl. 1977, 16, 299-311.
60. It is well-known from the literature that nucleophilic attack on π-allylpalladium complexes usually occurs on the less hindered carbon of the allyl system (see, for example, ref 1b and references therein). In the present case, however, the nucleophilic attack occurs exclusively at C-5 since it leads to a more stable double bond.
61. Nucleophilic attack by methanol occurs preferentially at the α-alkyl carbon owing to the partial aromatic character of the transition state leading to 6m or 7m.
62. Gabriele, B.; Salerno, G.; Costa, M.; Chiusoli, G. P. J. Mol. Catal. A 1996, 111, 43-48.
63. Beruben, D.; Marek, I.; Normant, J. F.: Platzer, N. J. Org. Chem. 1995, 60, 2488-2501.
64. Piotti, M. E.; Alper, H. J. Org. Chem. 1997, 62, 8484-8489.
65. Seiller, B.; Bruneau, C.; Dixneuf, P. H. Tetrahedron 1995, 51, 13089-13102.
66. McKeown, N. B.; Chambrier, I.; Cook, M. J. J. Chem. Soc., Perkin Trans. 1 1990, 1169-1177.
67. Alami, M.; Ferri, F.; Linstrumelle, G. Tetrahedron Lett. 1993, 34, 6403-6406.
68. Heyns, K.; Stute, R.; Scharmann, H. Tetrahedron 1966, 22, 2223-2235.