Carbon–carbon bond forming reactions mediated by cerium(IV) reagents

Abstract

Organic synthesis using carbon centred radicals generated by one electron oxidants is of current interest. Although Mn(OAc)₃ has received the most attention, it appears that cerium(IV) ammonium nitrate (CAN) would be a very useful reagent for the generation of radicals. The recent application of CAN in the construction of C–C bonds are highlighted in this review. CAN has been shown to mediate the facile oxidative addition of 1,3-dicarbonyl compounds to activated and unactivated alkenes leading to dihydrofurans and furanones. In most cases the reactions occur under milder conditions and the yields are superior when compared to Mn(OAc)₃ mediated reactions. The results available thus far suggest that CAN offers cast potential in radical mediated organic synthesis.

References

1. (a) For reviews see: B. Giese in Radicals in Organic Synthesis: Formation of Carbon–Carbon Bonds, Pergamon, Oxford, 1986;; D. H. R. Barton, Aldrichm. Acta, 1990, 23, 3; (b) D. P. Curran, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, New York, 1991, vol. 4, p. 715;; (c) A. L. J. Beckwith, Chem. Soc. Rev., 1993, 143; (d) P. I. Dalko, Tetrahedron, 1995, 51, 7579.
2. G. Stork and P. M. Sher, J. Am. Chem. Soc., 1983, 105, 6765 , and references therein..
3. M. Julia, Pure Appl. Chem., 1974, 40, 553.
4. A. L. J. Beckwith, Tetrahedron, 1981, 37, 3073 , and references therein..
5. C. Chatgilialoglu, K. U. Ingold and J. C. Scaiano, J. Am. Chem. Soc., 1981, 103, 7739 , and references therein..
6. G. Pattenden, A. J. Smithies, D. Tapolczy and D. S. Walter, J. Chem. Soc., Perkin Trans. 1, 1996, 7 and references therein..
7. L. Becking and H. J. Schafer, Tetrahedron Lett., 1988, 29, 280.
8. D. O. Cowan and R. L. Drisko, in Elements of Photochemistry, Plenum. New York, 1976..
9. W. J. De Klein, in Organic Synthesis by Oxidation with Metal Compounds, ed. W. J. Mijs and C. R. H. de Jonge, Plenum, New York, 1986, p. 261..
10. B. B. Snider, Chem. Rev., 1996, 96, 339 and references cited therein..
11. E. I. Heiba and R. M. Dessau, J. Am. Chem. Soc., 1972, 94, 2888.
12. E. I. Heiba, R. M. Dessau and P. G. Rodewald, J. Am. Chem. Soc., 1974, 96, 7977.
13. M. E. Kurz and P. Ngoviwatchai, J. Org. Chem., 1981, 46, 4672.
14. M. E. Kurz, V. Baru and P. N. Nguyen, J. Org. Chem., 1984, 49, 1603.
15. E. Baciocchi, R. Ruzziconi and D. D. Aira, Tetrahedron Lett., 1986, 27, 2763.
16. (a) E. Baciocchi and R. Ruzziconi, J. Org. Chem., 1986, 51, 1645; (b) E. Baciocchi and R. Ruzziconi, Gazz. Chim. Ital., 1986, 116, 671.
17. A. B. Paolobelli, P. Ceccherelli, F. Pizzo and R. Ruzziconi, J. Org. Chem., 1995, 60, 4954.
18. E. Baciocchi and R. Ruzziconi, Synth. Commun., 1988, 18, 1841.
19. E. Baciocchi, A. Casu and R. Ruzziconi, Synlett, 1990, 679.
20. A. B. Paolobelli, D. Latini and R. Ruzziconi, Tetrahedron Lett., 1993, 34, 721.
21. A. B. Paolobelli, F. Gioacchini and R. Ruzziconi, Tetrahedron Lett., 1993, 34, 6333.
22. J. R. Hwu, C. N. Chen and S. S. Shiao, J. Org. Chem., 1995, 60, 856.
23. K. Narasaka, T. Okauchi, K. Tanaka and M. Murakami, Chem. Lett., 1992, 2099.
24. N. Arai and K. Narasaka, Chem. Lett., 1995, 987.
25. V. Nair and J. Mathew, J. Chem. Soc., Perkin Trans. 1, 1995, 187.
26. J. lqbal, B. Bhatia and N. K. Nayyar, Tetrahedron, 1991, 47, 6457.
27. V. Nair, J. Mathew and K. V. Radhakrishnan, J. Chem. Soc., Perkin Trans. 1, 1996, 1487.
28. V. Nair, J. Mathew and S. Alexander, Synth. Commun., 1995, 25, 3981.
29. V. Nair and J. Mathew, J. Chem. Soc., Perkin Trans. 1, 1995, 1881.
30. E. Baciocchi, B. Giese, H. Farshchi and R. Ruzziconi, J. Org. Chem., 1990, 55, 5688.
31. V. Nair and J. Mathew, unpublished results..
32. R. Haller, R. Kohlmorgen and W. Hansel, Tetrahedron Lett., 1973, 15, 1205.
33. B. B. Snider and T. Kwon, J. Org. Chem., 1992, 57, 2399.
34. E. Baciocchi, R. Ruzziconi and A. B. Palolobelli, Tetrahedron, 1992, 48, 4617.
35. A. Citterio, R. Sebastiano and M. C. Carvayal, J. Org. Chem., 1991, 56, 5335.