Room-temperature hydrodebromination of 4,4'-dibromobiphenyl catalyzed by 1,1'-bis(diphenylphosphino) ferrocene complexes of palladium

Journal of Molecular Catalysis A: Chemical

Volumn 132, Issue 2-3, 1998, Pages 223-229

  Wei, Bing ^a   Hor, T S Andy ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Biphenyl; Bromobiphenyls; Debromination; Ferrocenyl phosphine; Palladiu; Reduction

Indexed keywords

EID: 0032526306     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1169(97)00274-4     Document Type: Article

References (66)

1. Loganathan B.G., Kannan K., Watanabe I., Kawano M., Irvine K., Kumar S., Sikka H.C. Environ. Sci. Technol. 29:1995;1832.
2. Kuehl D.W., Haebler R. Arch. Environ. Contam. Toxicol. 28:1995;494.
3. Bertrazzi P.A., Riboldi L., Pesatori A., Radice L., Zocchetti C. Am. J. Ind. Med. 11:1987;165.
4. National Research Council, Diet, Nutrition, and Cancer, Assembly of Life Sciences, National Academy Press, Washington, DC, 1982.
5. Sherman J.D. Toxicol. Ind. Health. 7:1991;197.
6. Kimbrough R.D., Groce D.F., Korver M.P., Burse V.W. J. Natl. Cancer Inst. 66:1981;535.
7. Blum A., Ames B. Science. 195:1977;12.
8. Dent J.G., Cagen S.Z., McCormack K.M., Rickert D.E., Gibson J.E. Life Sci. 20:1977;2075.
9. Dent J.G., Netter K.J., Gibson J.E. Toxicol. Appl. Pharmacol. 38:1976;237.
10. Harris S.J., Cecil H.C., Bitman J. Environ. Health Perspect. 23:1978;295.
11. Groce D.F., Kimbrough R.D. J. Toxicol. Environ. Health. 14:1984;695.
12. Corbett T.H., Beaudoin A.R., Cornell R.G., Anver M.R., Schumacher R., Endres J., Szwabowska M. Environ. Res. 10:1975;390.
13. Tilson H.A., Cabe P.A., Mitchell C.L. Environ. Health Perspect. 23:1978;257.
14. Selikoff I.J. Proc. R. Soc. London. 205:1979;153.
15. Kluwe W.M., McCormack K.M., Hook J.B. Environ. Health Perspect. 23:1978;241.
16. Andres J., Lambert I., Robertson L., Bandiera S., Sawyer T., Lovering S., Safe S. Toxicol. Appl. Pharmacol. 70:1983;204.
17. O'Keefe P.W. Environ. Health Perspect. 23:1978;283.
18. Abramowica D.A. Res. Microbiol. 145:1994;42.
19. Arbon R.E., Mincher B.J., Knighton W.B. Environ. Sci. Technol. 28:1994;2191.
20. Matsunaga K., Kondo M., Yamabe S., Mori T. Chemosphere. 27:1993;2317.
21. Fantoni R., Giardiniguidoni A., Mele A., Pizzela G., Teghil R. Proc. Indian Acad. Sci., Chem. Sci. 105:1993;735.
22. Bouquetsomrani C., Finiels A., Graffin P., Olive J.L. Appl. Catal. B, Environ. 8:1996;101.
23. Dolfing J., Beurskens J.E.M. Adv. Microbial Ecol. 14:1995;143.
24. Klasson K.T., Barton J.W., Evans B.S., Reeves M.E. Biotechnol. Prog. 12:1996;310.
25. Evans B.S., Dudley C.A., Klasson K.T. Appl. Biochem. Biotechnol. 57:1996;885.
26. Pellizari V.H., Bezborodnikov S., Quensen J.F., Tiedje J.M. Appl. Environ. Microbiol. 62:1996;2053.
27. Fava F., Digioia D., Marchetti L., Quattroni G. Appl. Microbiol. Biotechnol. 45:1996;562.
28. Dini P., Bart J.C.J., Giordano N. J. Chem. Soc., Perkin Trans. 2:1975;1479.
29. P.N. Pandey, M.L. Purkayastha, Synthesis (1982) 876.
30. Marques C.A., Selva M., Tundo P. J. Chem. Soc., Perkin Trans. 1. 4:1993;529.
31. Marques C.A., Selva M., Tundo P. J. Org. Chem. 58:1993;5256.
32. Marques C.A., Selva M., Tundo P. J. Org. Chem. 59:1994;3830.
33. C.A. Marques, O. Rogozhnikova, M. Selva, P. Tundo, J. Mol. Catal. A (1995) 301.
34. Baltzly R., Phillips A.P. J. Am. Chem. Soc. 68:1946;261.
35. Pri-Bar I., Buchman O. J. Org. Chem. 51:1986;734.
36. Akita Y., Inoue A., Ishida K., Terui K., Ohta A. Synth. Commun. 16:1986;1067.
37. Carfagna C., Musco A., Pontellini R. J. Mol. Catal. 54:1989;L23.
38. Ben-David Y., Gozin M., Portnoy M., Milstein D. J. Mol. Catal. 73:1992;173.
39. Lipowitz J., Bowman S.A. J. Org. Chem. 38:1973;162.
40. Akagah A., Poite J.C., Chanon M. Org. Prep. Prec. Int. 17:1985;219.
41. Paderes G.D., Metivier P., Jorgensen W.L. J. Org. Chem. 56:1991;4718.
42. Narisada M., Horibe I., Watanabe F., Takeda K. J. Org. Chem. 54:1989;5308.
43. Liu Y., Schwartz J., Cavallaro C.L. Environ. Sci. Technol. 29:1995;836.
44. Mayo F.R., Hurwitz M.D. J. Am. Chem. Soc. 71:1949;776.
45. K.-S. Gan, T.S.A. Hor, in: A. Togni, T. Hayashi (Eds.), Ferrocenes, VCH, Weinheim, Chap. 1, p. 48 and references therein, 1995.
46. Y. Xie, S.C. Ng, T.S.A. Hor, H.S.O. Chan, J. Chem. Res. (S) (1996) 150.
47. Hayashi T., Konishi M., Kobori Y., Kumada M., Higuchi T., Hirotsu K. J. Am. Chem. Soc. 106:1984;158.
48. B.P.S. Chauhan, Y. Tanaka, H. Yamashita, M. Tanaka, Chem. Commum. (1996) 1207.
49. Ishiyama T., Murate M., Miyaura N. J. Org. Chem. 60:1995;7508.
50. Brown J.M., Pereztorrente J.J., Alcock N.W., Clase H.J. Organometallics. 14:1995;207.
51. P.M. Maitlis, P. Espinet, M.J.H. Russell, in: G. Wilkinson, F.G.A. Stone, E.W. Abel (Eds.), Comprehensive Organometallic Chemistry: The Synthesis, Reactions and Structures of Organometallic Compounds, Pergamon, Oxford, Vol. 6 (1982) p. 250.
52. Parshall G.W. J. Am. Chem. Soc. 96:1974;2360.
53. Amatore C., Carré E., Jutand A., M'Barki M.A. Organometallics. 14:1995;1818.
54. Andrews G.C., Crawford T.C. Tetrahedron Lett. 21:1980;693.
55. Wei B., Li S., Lee H.K., Hor T.S.A. J. Organomet. Chem. 527:1997;133.
56. Sorrell T.N., Pearlman P.S. J. Org. Chem. 45:1980;3449.
57. Kubas G.J. Inorg. Synth. 19:1975;90.
58. G. Booth, J. Chatt, J. Chem. Soc. (1965) 3238.
59. Corain B., Longato B., Favero G., Ajò D., Pilloni G., Russo U., Kreissl F.R. Inorg. Chim. Acta. 157:1989;259.
60. Grim S.O., Keiter R.L., McFarlane W. Inorg. Chem. 6:1967;1133.
61. T.G. Appleton, M.A. Bennett, I.B. Tomkins, J. Chem. Soc., Dalton Trans. (1976) 439.
62. S. Li, B. Wei, P.M.N. Low, T.S.A. Hor, F. Xue, T.C.W. Mak, J. Chem. Soc., Dalton Trans. (1997) 1289.
63. S.-W.A. Fong, T.S.A. Hor, Proceedings of the Second USRP Congress, National University of Singapore (1994) p. 57.
64. Bishop J.J., Davison A., Katcher M.L., Merrill R.E., Smart J.C. J. Organomet. Chem. 27:1971;241.
65. R.F. Heck, Palladium Reagents in Organic Syntheses, Chap. 1, Academic Press, New York (1985) p. 1.
66. Wei B., Li S., Lee H.K., Hor T.S.A. J. Mol. Catal. A. 126:1997;L83.