Palladium-catalyzed cross-carbonylation of phenolic compounds with aldehydes to give benzofuran-2(3H)-one derivatives

Journal of Molecular Catalysis A: Chemical

Volumn 143, Issue 1-3, 1999, Pages 203-210

  Satoh, Tetsuya ^a   Tsuda, Takatoshi ^a   Terao, Yoshito ^a   Miura, Masahiro ^a   Nomura, Masakatsu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Aldehyde; Benzofuranone; Carbonylation; Palladium; Phenol

Indexed keywords

ALDEHYDE DERIVATIVE; BENZOFURAN 2(3H) ONE DERIVATIVE; BENZOFURAN DERIVATIVE; CARBONYL DERIVATIVE; NAPHTHOL DERIVATIVE; PALLADIUM; PHENOL DERIVATIVE; SALIGENIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; GAS LIQUID CHROMATOGRAPHY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0033536270     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1169(98)00388-4     Document Type: Article

References (36)

1. R. Anacardio, A. Arcadi, G. D'Anniballe, F. Marinelli, Synthesis (1995) 831 and references therein.
2. Ramachandran P.V., Chen G.-M., Brown H.C. Tetrahedron Lett. 37:1996;2205. and references therein.
3. H. Bahrmann, B. Cornils, C.D. Frohning, A. Mullen, in: J. Falbe (Ed.), New Syntheses with Carbon Monoxide, Springer, New York, 1980.
4. G. Wilkinson, F.G.A. Stone, E.W. Abel (Eds.), Comprehensive Organometallic Chemistry, Vol. 8, Pergamon, Oxford, 1982.
5. H.M. Colquhoun, J. Holton, D.J. Thompson, M.V. Twigg, New Pathways for Organic Synthesis, Plenum, New York, 1984.
6. H.M. Coloquhoun, D.J. Thompson, M.V. Twigg, Carbonylation, Plenum, New York, 1991.
7. Beller M., Cornils B., Frohnong C.D., Kohlpaintner C.W. J. Mol. Catal. A: Chemical. 104:1995;17.
8. Ali B.E., Okuro K., Vasapollo G., Alper H. J. Am. Chem. Soc. 118:1996;4264.
9. P. Kalck, R. Naigre, S. Sirol, FR2.721.926 (1996), Chem. Abstr., 124: 317531f.
10. Gabriele B., Salerno G., De Pascali F., Costa M., Chiusoli G.P. J. Chem. Soc., Perkin Trans. 1:1997;147.
11. Kablaoui N.M., Hicks F.A., Buchwald S.L. J. Am. Chem. Soc. 119:1997;4424.
12. Xiao W.-J., Alper H. J. Org. Chem. 62:1997;3422.
13. Sugioka T., Yoneda E., Onitsuka K., Zhang S.-W., Takahashi S. Tetrahedron Lett. 38:1997;4989.
14. Lee D.Y., Cho C.S., Jiang L.H., Wu X., Shim S.C., Oh D.H. Synth. Commun. 27:1997;3449.
15. Brunner M., Alper H. J. Org. Chem. 62:1997;7565.
16. Ogawa A., Kuniyasu H., Sonoda N., Hirao T. J. Org. Chem. 62:1997;8361.
17. Negishi E.-I., Makabe H., Shimoyama I., Wu G., Zhang Y. Tetrahedron. 54:1998;1095.
18. K. Itoh, M. Miura, M. Nomura, Tetrahedron Lett. (1992) 5369.
19. Satoh T., Kokubo K., Miura M., Nomura M. Organometallics. 13:1994;4431.
20. Satoh T., Ikeda M., Miura M., Nomura M. J. Mol. Catal. A: Chemical. 111:1996;25.
21. T. Satoh, T. Itaya, M. Miura, M. Nomura, Chem. Lett. (1996) 823.
22. Satoh T., Ikeda M., Kushino Y., Miura M., Nomura M. J. Org. Chem. 62:1997;2662.
23. M. Miura, T. Tsuda, T. Satoh, M. Nomura, Chem. Lett. (1997) 1103.
24. Satoh T., Tsuda T., Kushino Y., Miura M., Nomura M. J. Org. Chem. 61:1996;6476. A preliminary communication of this work.
25. R.F. Heck, Palladium Reagents in Organic Syntheses, Academic Press, New York, 1985.
26. Talley J.J., Evans I.A. J. Org. Chem. 49:1984;5267.
27. Piccolo O., Filippini L., Tinucci L., Valoti E., Citterio A. Tetrahedron. 42:1986;885.
28. Watanabe M., Date M., Kawanishi K., Hori T., Furukawa S. Chem. Pharm. Bull. 39:1991;41.
29. Bistrzycki A., Flatau J. Ber. 28:1895;989.
30. Martini J.C., Franke N.W., Singerman G.M. J. Org. Chem. 35:1970;2904.
31. W. Nagata, K. Okada, T. Aoki, Synthesis (1979) 365.
32. Tamaru Y., Yamada Y., Inoue K., Yamamoto Y., Yoshida Z. J. Org. Chem. 48:1983;1286.
33. Trost B.M., Toste F.D. J. Am. Chem. Soc. 118:1996;6305.
34. Cavinato G., Toniolo L. J. Mol. Catal. 78:1993;9.
35. Lin Y.-S., Yamamoto A. Bull. Chem. Soc. Jpn. 71:1998;723.
36. Kushino Y., Itoh K., Miura M., Nomura J. Mol. Catal. 89:1994;151.