The selective functionalization of saturated hydrocarbons: Recent developments in Gif chemistry

Pure and Applied Chemistry

Volumn 69, Issue 9, 1997, Pages 1941-1950

  Barton, Derek H R ^a   Hu, Bin ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001161606     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199769091941     Document Type: Article

References (51)

1. (a) Olah, G.A.; Molnár, Á. Hydrocarbon Chemistry; John Wiley & Sons: New York, 1995.
2. (b) The Activation of Dioxygen and Homogeneous Catalytic Oxidation, Barton, D.H.R.; Martell, A.E.; Sawyer, D.T. Eds.; Plenum: New York, 1993.
3. (c) Shilov, A.E. Activation of Saturated Hydrocarbons by Transition Metal Complexes; D. Reidel Publishing Co., Dordrecht, The Netherlands, 1984.
4. (d) Activation and Functionalization of Alkanes; Hill, C.L. Ed.; John Wiley & Sons: New York, 1989.
5. (a) Akhtar, M.; Wright, J.N. Nat. Proc. Report 1991, 527.
6. (b) Cytochrome P-450: Structure, Mechanism and Biochemistry; Ortiz de Montellano, P.R. Ed., Plenum Press: New York, 1986.
7. (c) Relationships between Structure and Function of Cytochrome P-450 - Experiments, Calculations, Models; Ruchpaul K; Rein, H. Eds., Akademie Verlag: Berlin, 1992,
8. (a) Rosenzweig, A.C.; Frederick, C.A.; Lippard, S.J.; Nordlund, P. Nature 1993, 366, 537.
9. (b) Rosenzweig, A.C.; Nordlund, P.; Takahara, P.M.; Frederick, C.A.; Lippard, S.J. Chemistry & Biology 1995, 2, 409.
10. Reddy, C.C.; Hamilton, G.A.; Madyastha, K.M. in Biological Oxidation Systems, Academic Press: San Diego, California, 1990, Vol. I, , pp xix.
11. (a) Green, J.; Dalton, H. J. Biol. Chem. 1989, 264, 17698.
12. (b) Fox, B.G.; Lipscomb, J.D. in Biological Oxidation systems; Reddy, C.C.; Hamilton, G.A.; Madyasha, K.M. Eds, Academic Press: San Diego, California, 1990, Vol. I, pp 367.
13. (c) Feig, A.L.; Lippard, S.J. Chem. Rev. 1994, 94, 759.
14. (a) Barton, D.H.R.; Gastiger, M.J.; Motherwell, W.B. J. Chem. Soc., Chem. Commun. 1983, 41.
15. (b) Barton, D.H.R.; Gastiger, M.J.; Motherwell, W.B. J. Chem. Soc., Chem. Commun. 1983, 731.
16. (c) Balavoine, G.; Barton, D.H.R.; Boivin, J.; Gref, A.; Ozbalik, N.; Rivière, H. Tetrahedron Lett. 1986, 27, 2849.
17. (d) Barton, D.H.R.; Boivin, J.; Motherwell, W.B.; Ozbalik, N.; Schwartzentruber, K.M.; Jankowski, K. New J. Chem. 1986, 10, 387.
18. (e) Barton, D.H.R.; Halley, F.; Ozbalik, N.; Young, E. New J. Chem. 1989, 13, 177.
19. (f) Barton, D.H.R.; Halley, F.; Ozbalik, N.; Schmitt, M.; Young, E.; Balavoine, G. J. Am. Chem. Soc. 1989, 111, 7144.
20. (g) About-Jaudet, E.; Barton, D.H.R.; Csuhai, E.; Ozbalik, N. Tetrahedron Lett. 1990, 31, 1657.
21. For other significant contributions to Gif Chemistry see: (a) Tung, H.-C; Kang, C.; Sawyer, D.T. J. Am. Chem. Soc. 1992, 114, 3445 and references cited therein. (b) Schuchardt, U.; Carvalho, W.A.; Spinacé. E.V. Synlett 1993, 713 and references cited therein. Briffaud, T.; Larpent, C.; Patin, H. J. Chem. Soc., Chem. Commun. 1990, 1193. Lee, K.-W.; Kim, S.-B.; Jun, K.-W.; Shim, E.-K. New J. Chem. 1993, 17, 409 and references therein.
22. For other significant contributions to Gif Chemistry see: (a) Tung, H.-C; Kang, C.; Sawyer, D.T. J. Am. Chem. Soc. 1992, 114, 3445 and references cited therein. (b) Schuchardt, U.; Carvalho, W.A.; Spinacé. E.V. Synlett 1993, 713 and references cited therein. Briffaud, T.; Larpent, C.; Patin, H. J. Chem. Soc., Chem. Commun. 1990, 1193. Lee, K.-W.; Kim, S.-B.; Jun, K.-W.; Shim, E.-K. New J. Chem. 1993, 17, 409 and references therein.
23. For other significant contributions to Gif Chemistry see: (a) Tung, H.-C; Kang, C.; Sawyer, D.T. J. Am. Chem. Soc. 1992, 114, 3445 and references cited therein. (b) Schuchardt, U.; Carvalho, W.A.; Spinacé. E.V. Synlett 1993, 713 and references cited therein. (c) Briffaud, T.; Larpent, C.; Patin, H. J. Chem. Soc., Chem. Commun. 1990, 1193. Lee, K.-W.; Kim, S.-B.; Jun, K.-W.; Shim, E.-K. New J. Chem. 1993, 17, 409 and references therein.
24. For other significant contributions to Gif Chemistry see: (a) Tung, H.-C; Kang, C.; Sawyer, D.T. J. Am. Chem. Soc. 1992, 114, 3445 and references cited therein. (b) Schuchardt, U.; Carvalho, W.A.; Spinacé. E.V. Synlett 1993, 713 and references cited therein. Briffaud, T.; Larpent, C.; Patin, H. J. Chem. Soc., Chem. Commun. 1990, 1193. (d) Lee, K.-W.; Kim, S.-B.; Jun, K.-W.; Shim, E.-K. New J. Chem. 1993, 17, 409 and references therein.
25. Barton, D.H.R.; Doller, D. Acc. Chem. Res. 1992, 25, 504.
26. Barton, D.H.R.; Bévière, S.D.; Chavasiri, W.; Csuhai, E.; Doller, D.; Liu, W.G. J. Am. Chem. Soc. 1992, 114, 2147.
27. Barton, D.H.R.; Csuhai, E.; Doller, D.; Balavoine, G. J. Chem. Soc., Chem. Commun. 1990, 1787.
28. Barton, D.H.R.; Bévière, S.D.; Doller, D. Tetrahderon Lett. 1991, 32, 4671.
29. Knight, C.; Perkins, M.J. J. Chem. Soc., Chem. Commun. 1991, 925.
30. (a) Barton, D.H.R.; Bévière, S.D.; Chavasiri, W.; Doller, D.; Liu, W.G.; Reibenspies, J.H. New J. Chem. 1992, 16, 1019.
31. (b) Sawyer, D.T.; Kang, C.; Llobet, A.; Redman, C. J. Am, Chem. Soc. 1993, 115, 5817.
32. Barton, D.H.R.; Halley, F.; Ozbalik, N.; Schmitt, M.; Young, E.; Balavoine, G. J. Am. Chem. Soc. 1989, 111, 7144.
33. Barton, D.H.R.; Csuhai, E.; Ozbalik, N. Tetrahedron 1990, 46, 3743.
34. (a) Clark, L.J. Analytical Chemistry 1962, 34, 348.
35. (b) Pollock, E.N.; Miguel, A.N. Analytical Chemistry 1967, 39, 272.
36. Bardin, C.; Barton, D.H.R.; Hu, B.; Rojas-Wahl, R.U.; Taylor, D.K. Tetrahedron Lett. 1994, 35, 5805.
37. Barton, D.H.R.; Chabot, B.; Delanghe, N.C.; Hu, B.; LeGloahec, V.N.; Rojas Wahl, R.U. Tetrahedron Lett. 1995, 36, 7007.
38. Barton, D.H.R.; Chabot, B.M.; Hu, B. Tetrahedron Lett. 1996, 37, 1755.
39. Barton, D.H.R.; Chabot, B.M.; Hu, B. Tetrahedron, in press.
40. The same conclusions for similar systems are abundant in the literature. See for example: (a) Groves, J.T.; Van Der Puy, M. J. Am. Chem. Soc. 1976, 98, 5290. (b) Sawyer, D.T.; Hage, J.P.; Sobkowiak, A. J. Am. Chem. Soc. 1995, 117, 106. Hage, J.P.; Llobet, A.; Sawyer, D.T. Bioorg. Med. Chem. 1995, 3, 1383. Wink, D.A.; Nims, R.W.; Saavedra, J.E.; Utermajlen, W.E., Jr.; Ford, P.C. Proc. Natl. Acad. Sci. USA 1994, 91, 6604.
41. The same conclusions for similar systems are abundant in the literature. See for example: (a) Groves, J.T.; Van Der Puy, M. J. Am. Chem. Soc. 1976, 98, 5290. (b) Sawyer, D.T.; Hage, J.P.; Sobkowiak, A. J. Am. Chem. Soc. 1995, 117, 106. Hage, J.P.; Llobet, A.; Sawyer, D.T. Bioorg. Med. Chem. 1995, 3, 1383. Wink, D.A.; Nims, R.W.; Saavedra, J.E.; Utermajlen, W.E., Jr.; Ford, P.C. Proc. Natl. Acad. Sci. USA 1994, 91, 6604.
42. The same conclusions for similar systems are abundant in the literature. See for example: (a) Groves, J.T.; Van Der Puy, M. J. Am. Chem. Soc. 1976, 98, 5290. (b) Sawyer, D.T.; Hage, J.P.; Sobkowiak, A. J. Am. Chem. Soc. 1995, 117, 106. (c) Hage, J.P.; Llobet, A.; Sawyer, D.T. Bioorg. Med. Chem. 1995, 3, 1383. Wink, D.A.; Nims, R.W.; Saavedra, J.E.; Utermajlen, W.E., Jr.; Ford, P.C. Proc. Natl. Acad. Sci. USA 1994, 91, 6604.
43. The same conclusions for similar systems are abundant in the literature. See for example: (a) Groves, J.T.; Van Der Puy, M. J. Am. Chem. Soc. 1976, 98, 5290. (b) Sawyer, D.T.; Hage, J.P.; Sobkowiak, A. J. Am. Chem. Soc. 1995, 117, 106. Hage, J.P.; Llobet, A.; Sawyer, D.T. Bioorg. Med. Chem. 1995, 3, 1383. (d) Wink, D.A.; Nims, R.W.; Saavedra, J.E.; Utermajlen, W.E., Jr.; Ford, P.C. Proc. Natl. Acad. Sci. USA 1994, 91, 6604.
44. Walling, C. Acc. Chem. Res. 1975, 8, 125.
45. Edwards, J.O.; Curci, R. Fenton Type Activation and Chemistry of Hydroxyl Radical. In Catalytic Oxidations with Hydrogen Peroxide as Oxidant; Strukul, G. Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1992, pp 97.
46. Rudakov, E.S.; Volkova, L.K.; Tret'yakov, V.P.; Zamashchikov, V.V. Kinetics and Catalysis (Engl. Trans) 1982, 23, 18.
47. Barton, D.H.R.; Hu, B.; Taylor, D.K.; Rojas Wahl, R.U. J. Chem. Soc., Perkin Trans. 2, in press.
48. Barton, D.H.R.; Hu, B.; Rojas Wahl, R.U.; Taylor, D.K. New J. Chem. 1996, 20, 121.
49. (a) Kasler, F. Quantitative Analysis by NMR Spectroscopy, Academic: New York, 1973, Ch. 14.
50. (b) Levy, G.C.; Lichter, R.L.; Nelson, G.L. Carbon-13 Nuclear Magnetic Resonance Spectroscopy, John Wiley & Sons: New York, 1980.
51. 3. See for reactivity comparison of three examples: Dong, Y.; Ménage, S.; Brennan, B.A.; Elgreen, T.E.; Jang, H.G.; Pearce, L.L.; Que, L., Jr. J. Am. Chem. Soc. 1993, 115, 1851.