Synthesis of naphthofuran-2(3H)-one derivatives by palladium-catalyzed three-component coupling using naphthols, aldehydes, and carbon monoxide

Journal of Organic Chemistry

Volumn 61, Issue 19, 1996, Pages 6476-6477

  Satoh, Tetsuya ^a   Tsuda, Takatoshi ^a   Kushino, Yuichi ^a   Miura, Masahiro ^a   Nomura, Masakatsu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029819848     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9610873     Document Type: Article

References (16)

1. (a) Anacardio, R.; Arcadi, A.; D'Anniballe, G.; Marinelli, F. Synthesis 1995, 831 and references therein.
2. (b) Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1996, 37, 2205 and references therein.
3. (a) Bahrmann, H.; Cornils, B.; Frohning, C. D.; Mullen, A. New Syntheses with Carbon Monoxide; Falbe, J., Ed.; Springer-Verlag: New York, 1980.
4. (b) Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 8.
5. (c) Colquhoun, H. M.; Holton, J.; Thompson, D. J.; Twigg, M. V. New Pathways for Organic Synthesis; Plenum: New York, 1984.
6. (d) Coloquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum: New York, 1991.
7. (a) Okuro, K.; Furuune, M.; Miura, M.; Nomura, M. J. Org. Chem. 1993, 58, 7606.
8. (b) Miura, M.; Enna, M.; Okuro, K.; Nomura, M. J. Org. Chem. 1995, 60, 4999.
9. (c) Satoh, T.; Itaya, T.; Okuro, K.; Miura, M.; Nomura, M. J. Org. Chem. 1995, 60, 7267.
10. In the reaction with 2b, a small amount of aldol type dimerization product (<10%) of the aldehyde was detected by GC-MS, suggesting that the side reaction is not significant.
11. Such a reaction of phenolic compounds with aldehydes is well-known to be catalyzed by acidic species including carboxylic acids, e.g.: (a) Martini, J. C.; Franke, N. W.; Singerman, G. M. J. Org. Chem. 1970, 35, 2904. (b) Nagata, W.; Okada, K.; Aoki, T. Synthesis 1979, 365.
12. Such a reaction of phenolic compounds with aldehydes is well-known to be catalyzed by acidic species including carboxylic acids, e.g.: (a) Martini, J. C.; Franke, N. W.; Singerman, G. M. J. Org. Chem. 1970, 35, 2904. (b) Nagata, W.; Okada, K.; Aoki, T. Synthesis 1979, 365.
13. 3) could also catalyze the initial reaction.
14. In contrast to alcohol 6, its carboxylate derivatives and α-aryl-ethyl bromides have been reported to be capable of being carbonylated in the presence of palladium catalysts: (a) Baird, J. M.; Kern, J. R.; Lee, G. R.; Morgans, D. J.; Sparacino, M. L. J. Org. Chem. 1991, 56, 1928. (b) Arzoumanian, H.; Buono, G.; Choukrad, M.; Petrignani, J.-F. Organometallics 1988, 7, 59.
15. In contrast to alcohol 6, its carboxylate derivatives and α-aryl-ethyl bromides have been reported to be capable of being carbonylated in the presence of palladium catalysts: (a) Baird, J. M.; Kern, J. R.; Lee, G. R.; Morgans, D. J.; Sparacino, M. L. J. Org. Chem. 1991, 56, 1928. (b) Arzoumanian, H.; Buono, G.; Choukrad, M.; Petrignani, J.-F. Organometallics 1988, 7, 59.
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