Rhodium-catalysed cyclic carbonylation of 2-alkynylphenols: synthesis of benzofuranones and coumarins

Abstract

Rhodium-catalysed carbonylation of 2-alkynylphenols 1 under water-gas shift reaction conditions gives benzofuranone derivatives 2 and coumarin derivatives 3 in high yield (up to 96%, 2∶3 = 65∶35), in which the hydroxy group adjacent to the carbon–carbon triple bond participitates in the cyclic carbonylation.

References

1. P. Pino and G. Braca, Organic Synthesis via Metal Carbonyls, ed. I. Wender and P. Pino, Wiley, New York, 1977, vol. 2, p. 419.
2. G. W. Parshall and S. D. Ittel, Homogeneous Catalysis, The Application and Chemistry of Catalysis by Soluble Transition Metal Complexes, Wiley-Interscience, New York, 2nd edn., 1992, p. 93.
3. I. Tkatchenko, in Comprehensive Organometallic Chemistry, ed. G. Wilkinson, F. G. A. Stone and E. Abel, Pergamon Press, Oxford, 1982, vol. 8, p. 101.
4. W. Reppe and H. Vetter, Justus Liebigs Ann. Chem., 1953, 121, 582.
5. H. C. Kang, C. H. Mauldin, K. Cann and R. Pettit, J. Am. Chem. Soc., 1977, 99, 8323.
6. A. D. King, D. B. King and D. B. Yang, J. Am. Chem. Soc., 1980, 102, 1028.
7. C. Ungermann, V. Landis, S. A. Moya, H. Walker, R. G. Rinker and P. C. Ford, J. Am. Chem. Soc., 1979, 101, 5922.
8. J. C. Bricker, C. C. Nagel and S. G. Shore, J. Am. Chem. Soc., 1982, 104, 1444.
9. P. Hong and H. Yamazaki, Chem. Lett., 1981, 989.
10. H. Urata and T. Fuchikami, Chem. Lett., 1987, 833.
11. I. Matsuda, T. Sakakibara, H. Inoue and H. Nagashima, Tetrahedron Lett., 1992, 33, 5799.
12. K. Kudo, Y. Oida, K. Mitsuhashi, S. Mori, K. Komatsu and N. Sugita, Bull. Chem. Soc. Jpn., 1996, 69, 1337.
13. B. E. Ali, K. Okuro, G. Vasapollo and H. Alper, J. Am. Chem. Soc., 1996, 118, 4264.
14. J. Tsuji and T. Nogi, J. Am. Chem. Soc., 1966, 88, 1289.
15. H. Alper, J. K. Courrie and H. D. Abbayes, J. Chem. Soc., Chem. Commun., 1978, 311.
16. R. M. Laine and E. J. Crawford, J. Mol. Catal., 1988, 44, 357.
17. G. Cavinato and L. Toniolo, J. Mol. Catal., 1996, 105, 9.
18. T. Joh, K. Fujiwara and S. Takahashi, Bull. Chem. Soc. Jpn., 1993, 66, 978.
19. Y. Joh, K. Doyama, K. Fujiwara, K. Maeshima and S. Takahashi, Organometallics, 1991, 10, 508.
20. K. Joh, K. Doyama, T. Onitsuka, S. Shiohara and S. Takahashi, Organometallics, 1991, 10, 2493.
21. K. Hirao, N. Morii, T. Joh and S. Takahashi, Tetrahedron Lett., 1995, 36, 6243.
22. T. Sugioka, S.-W. Zhang, N. Morii, T. Joh and S. Takahashi, Chem. Lett., 1966, 249.
23. S. Takahashi, Y. Kuroyama, K. Sonogashira and N. Hagihara, Synthesis, 1980, 627.
24. P. Sosa, C. Alagon, M. Martin and D. Possani, Biochemistry, 1986, 25, 2927.
25. F. Dean and R. Varma, J. Chem. Soc., Perkin Trans. 1, 1982, 1193.
26. M. Cowie and R. S. Dickson, Inorg. Chem., 1981, 20, 2682.
27. Y. J. Kim, K. Osakada, A. Takenaka and A. Yamamoto, J. Am. Chem. Soc., 1990, 112, 1096.
28. Y. J. Kim, K. Osakada, K. Sugita, T. Yamamoto and A. Yamamoto, Organometallics, 1988, 7, 2182.
29. Y. Kondo, T. Sakamoto and H. Yamasaki, Heterocycles, 1989, 29, 1013.
30. N. Kaneta and M. Mori, Chem. Lett., 1995, 627.
31. Y. Ming and W. D. Boykin, Heterocycles, 1987, 26, 3229.
32. J. Andrieux and D. Molho, Bull. Soc. Chim. Fr., 1977, 1187.
33. K. Swiss and W. Hinkiy, Synthesis, 1992, 127.
34. R. C. Larock and L. W. Harrison, J. Am. Chem. Soc., 1984, 106, 4218.