Copper-catalyzed homolytic and heterolytic benzylic and allylic oxidation using tert-butyl hydroperoxide

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 11, 1998, Pages 2429-2434

  Rothenberg, Gadi ^a   Feldberg, Liron ^a   Wiener, Harold ^a   Sasson, Yoel ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038061521     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a805324c     Document Type: Article

References (41)

1. D. T. Sawyer, A. Sobkowiak and T. Matsushita, Acc. Chem. Res., 1996, 9, 409.
2. C. Walling, Acc. Chem. Res., 1998, 31, 155.
3. P. A. MacFaul, D. D. M. Wayner and K. U. Ingold, Acc. Chem. Res., 1998, 31, 159.
4. (a) For a monograph on oxidation reactions, see R. A. Sheldon and J. K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981;
5. (b) for recent studies on the oxidation of allylic and benzylic alcohols, see K. P. Peterson and R. C. Larock, J. Org. Chem., 1998, 63, 3185, and refs. cited therein.
6. (a) H. H. Szmant, Organic Building Blocks of the Chemical Industry, Wiley, New York, 1989, pp. 386-391;
7. (b) M. D. Clayton, Z. Marcinow and P. W. Rabideau, J. Org. Chem., 1996, 61, 6052.
8. (a) M. Nakayama, S. Shinke, Y. Matsushita, S. Ohira and S. Hayashi, Bull. Chem. Soc. Jpn., 1979, 52, 184;
9. (b) W. G. Dauben, M. Lorber and D. S. Fullerton, J. Org. Chem., 1969, 34, 3587;
10. (c) E. J. Parish, S. Chitrakorn and T.-Y. Wei, Synth. Commun., 1986, 16, 1371.
11. (a) K. B. Sharpless and T. R. Verhoeven, Aldrichim. Acta. 1979, 12, 63;
12. (b) J. Muzart and A. Naît-Ajjou, J. Mol. Catal., 1991, 66, 155;
13. (c) Synthesis, 1993, 785;
14. (d) J. Muzart, Tetrahedron Lett., 1986, 27, 3139;
15. (e) 1987, 28, 2131;
16. (f) S. Uemura and S. R. Patil, Tetrahedron Lett., 1982, 23, 4353;
17. (g) J. A. R. Salvador, M. L. Sa e Melo and A. S. C. Neves, Tetrahedron Lett., 1997, 38, 119.
18. (a) I. E. Marko, P. R. Giles, M. Tsukazaki, S. M. Brown and C. J. Urch, Science, 1996, 274, 2044;
19. (b) J. Muzart, J. Mol. Catal., 1991, 64, 381.
20. (a) M. T. Rispens, C. Zondervan and B. L. Feringa, Tetrahedron: Asymmetry, 1995, 6, 661;
21. (b) A. Levina and J. Muzart, Tetrahedron: Asymmetry, 1995, 6, 147;
22. (c) Z.-R. Lu, Y.-Q. Yin and D.-S. Jin, J. Mol. Catal., 1991, 70, 391.
23. Preliminary communication: L. Feldberg and Y. Sasson, J. Chem. Soc., Chem. Commun., 1994, 1807.
24. cf. (a) R. A. Miller, W. Li and G. R. Humphrey, Tetrahedron Lett., 1996, 37, 3429; (b) M. Harre, R. Haufe, K. Nickish, P. Weinig, H. Weinmann, W. A. Kinney and X. Zhang, Org. Proc. Res. Dev., 1998, 2, 100; (c) G. Rothenberg, H. Wiener and Y. Sasson, J. Mol. Catal., 1998, 136, 251; (d) See also J. Muzart and A. Naît-Ajjou, in The Activation of Dioxygen and Homogenous Catalytic Oxidation, D. H. R. Barton, A. R. Martell and D. T. Sawyer, ed., Plenum Press, New York, 1993, p. 471.
25. cf. (a) R. A. Miller, W. Li and G. R. Humphrey, Tetrahedron Lett., 1996, 37, 3429; (b) M. Harre, R. Haufe, K. Nickish, P. Weinig, H. Weinmann, W. A. Kinney and X. Zhang, Org. Proc. Res. Dev., 1998, 2, 100; (c) G. Rothenberg, H. Wiener and Y. Sasson, J. Mol. Catal., 1998, 136, 251; (d) See also J. Muzart and A. Naît-Ajjou, in The Activation of Dioxygen and Homogenous Catalytic Oxidation, D. H. R. Barton, A. R. Martell and D. T. Sawyer, ed., Plenum Press, New York, 1993, p. 471.
26. cf. (a) R. A. Miller, W. Li and G. R. Humphrey, Tetrahedron Lett., 1996, 37, 3429; (b) M. Harre, R. Haufe, K. Nickish, P. Weinig, H. Weinmann, W. A. Kinney and X. Zhang, Org. Proc. Res. Dev., 1998, 2, 100; (c) G. Rothenberg, H. Wiener and Y. Sasson, J. Mol. Catal., 1998, 136, 251; (d) See also J. Muzart and A. Naît-Ajjou, in The Activation of Dioxygen and Homogenous Catalytic Oxidation, D. H. R. Barton, A. R. Martell and D. T. Sawyer, ed., Plenum Press, New York, 1993, p. 471.
27. cf. (a) R. A. Miller, W. Li and G. R. Humphrey, Tetrahedron Lett., 1996, 37, 3429; (b) M. Harre, R. Haufe, K. Nickish, P. Weinig, H. Weinmann, W. A. Kinney and X. Zhang, Org. Proc. Res. Dev., 1998, 2, 100; (c) G. Rothenberg, H. Wiener and Y. Sasson, J. Mol. Catal., 1998, 136, 251; (d) See also J. Muzart and A. Naît-Ajjou, in The Activation of Dioxygen and Homogenous Catalytic Oxidation, D. H. R. Barton, A. R. Martell and D. T. Sawyer, ed., Plenum Press, New York, 1993, p. 471.
28. For a monograph on the fundamentals of PTC, see C. M. Starks, C. L. Liotta and M. Halpern, Phase-Transfer Catalysis, Chapman and Hall, New York, 1994.
29. For a review on PTC extraction by hydrogen-bonding, see Y. Sasson and R. Neumann, in Handbook of Phase Transfer Catalysis, Y. Sasson and R. Neumann, ed., Chapman and Hall, London, 1997, pp. 510-546.
30. J. B. Sharkey and S. Z. Lewin, Thermochim. Acta. 1972, 3, 189.
31. I. W. C. E. Arends, K. U. Ingold and J. Lusztyk, J. Am. Chem. Soc., 1993, 115, 466.
32. Preliminary communication: L. Feldberg and Y. Sasson. Tetrahedron Lett., 1996, 12, 2063.
33. (a) J. K. Kochi, Tetrahedron, 1962, 18, 483;
34. (b) J. Am. Chem. Soc., 1962, 84, 1572.
35. (a) F. Minisci, F. Fontana, S. Araneo, F. Recupero, S. Banfi and S. Quici, J. Am. Chem. Soc., 1995, 117, 226;
36. (b) F. Minisci, F. Fontana, S. Araneo, F. Recupero and L. Zhao, Synlett, 1996, 119.
37. H. Paul, R. D. Small and J. C. Scaiano, J. Am. Chem. Soc., 1978, 102, 4520.
38. E. Napadensky and Y. Sasson, J. Chem. Soc., Chem. Commun., 1991, 65.
39. Similar transient high oxidation state copper species have been envisaged: (a) D. H. R. Barton, S. D. Bévière, W. Chavasiri, É. Csuhai and D. Doller, Tetrahedron, 1992, 48, 2895;
40. (b) S.-I. Murahashi, Y. Oda, T. Naota and M. Komiya, J. Chem. Soc., Chem. Commun., 1993, 139.
41. J. Muzart and A. Naît-Ajjou, J. Mol. Catal., 1994, 92, 277.