Bromination of phenols in bromoperoxidase-catalyzed oxidations

Tetrahedron

Volumn 68, Issue 46, 2012, Pages 9456-9463

  Wischang, Diana ^a   Hartung, Jens ^a  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

Aromatic substitution; Ascophyllum nodosum; Bromine; Bromoperoxidase; Hammett correlation; Hypobromous acid; Linear free energy relationship; Phenol; Tribromide

Indexed keywords

BROMIDE ION; BROMINE; BROMOPEROXIDASE; BUTANOL; CHLORIDE; ELECTROPHILE; ETHANE; HYDROGEN; HYDROGEN PEROXIDE; MORPHOLINE DERIVATIVE; PEROXIDASE; PHENOL DERIVATIVE; SODIUM BROMIDE; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; VANADIC ACID;

ARTICLE; ASCOPHYLLUM; ASCOPHYLLUM NODOSUM; BROMINATION; CATALYSIS; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; NONHUMAN; OXIDATION; PH; PRIORITY JOURNAL; THERMODYNAMICS;

ASCOPHYLLUM NODOSUM; PHAEOPHYCEAE;

EID: 84867049900     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.08.081     Document Type: Article

References (64)

1. R. Frim, and S.D. Ukeles J.E. Kogel, N.C. Trived, J.M. Baker, Industrial Minerals & Rocks 7th ed. 2006 Society for Mining, Metallurgy, and Exploration Littleton, Colorado 285 294
2. A.F. Hollemann, and N. Wiberg Lehrbuch der Anorganischen Chemie 102nd ed. 2007 Walter de Gruyter Berlin 438-440
3. D. Wischang, O. Brücher, and J. Hartung Coord. Chem. Rev. 255 2011 2204 2217
4. R.J. Salawitch Nature 439 2006 275 277
5. P.B.D. De la Mare, and B.E. Swedlund S. Patai, The Chemistry of Functional Groups. The Chemistry of the Carbon-Halogen Bond 1973 Wiley Chichester, UK 407 548
6. Y. Sasson S. Patai, Z.Z. Rappoport, The Chemistry of Functional Groups. Supplement D2, The Chemistry of Halides, Pseudo-Halides, and Azides 1995 Wiley Chichester, UK 535 628
7. S.-L. Neidleman, and J. Geigert Biohalogenation, Principles, Basic Roles and Application 1986 Ellis Horwood Chichester, UK
8. J.W. Blunt, B.R. Copp, W.-P. Hu, M.H.G. Munro, P.T. Northcote, and M.R. Prinsep Nat. Prod. Rep. 26 2009 170 244
9. G.W. Gribble Naturally Occuring Organohalogen Compounds. A Comprehensive Update A.D. Kinghorn, H. Falk, J. Kobayashi, Progress in the Chemistry of Organic Natural Products Vol. 91 2010 Springer Wien
10. J. Hartung, Y. Dumont, M. Greb, D. Hach, F. Köhler, H. Schulz, M. Časný, D. Rehder, and H. Vilter Pure Appl. Chem. 81 2009 1251 1264
11. A. Butler Coord. Chem. Rev. 187 1999 17 35
12. For a review on biohalogenation: F.H. Vaillancourt, E. Yeh, D.A. Vosburg, S. Garneau-Tsodikova, and C.T. Walsh Chem. Rev. 106 2006 3364 3378
13. A. Butler, and J.V. Walker Chem. Rev. 93 1993 1937 1944
14. H. Vilter Vanadium and Its Role in Life H. Sigel, A. Sigel, Metal Ions in Biological Systems Vol. 31 1995 Dekker New York, NY 325 362
15. D. Wischang, and J. Hartung Tetrahedron 67 2011 4045 4048
16. O. Bortolini, M. Carraro, V. Conte, and S. Moro Eur. J. Inorg. Chem. 2003 42 46
17. R. Wever, M.G.M. Tromp, B.E. Krenn, A. Marjani, and M. von Tol Environ. Sci. Technol. 25 1991 446 449
18. 2, catalyzed by molybdate(VI) or vanadate(V) at pH 1.1 in chloroform/water in the presence of adamantylideneadamantane, see: O. Bortolini, C. Chiappa, V. Conte, and M. Carraro Eur. J. Org. Chem. 1999 3237 3239
19. G.A. Olah, B.G.B. Gupta, R. Malhotra, and S.C. Narang J. Org. Chem. 45 1980 1638 1639
20. gp=0): R.T. Sanderson Science 121 1955 207 208
21. S.G. Bratsch J. Chem. Educ. 62 1985 101 103
22. G. Belluci, R. Bianchini, R. Ambrosetti, and G. Ingrosso J. Org. Chem. 50 1985 3313 3318
23. G. Belluci, R. Bianchini, and S. Vecchiani J. Org. Chem. 51 1986 4224 4232
24. R.S. Brown, H. Slebocka-Tilk, A.J. Bennet, G. Bellucci, R. Bianchini, and R. Ambrosetti J. Am. Chem. Soc. 112 1990 6310 6316
25. W.J. Wilson, and F.G. Soper J. Chem. Soc. 1949 3376 3379
26. J.A. Vona, and P.C. Merker J. Org. Chem. 14 1949 1048 1050
27. M. Eigen, and K. Kustin J. Am. Chem. Soc. 84 1962 1355 1361
28. J.M. Pink Can. J. Chem. 48 1970 1169 1171
29. D.B. Scaife, and H.J.V. Tyrrell J. Chem. Soc. 80 1958 386 392
30. L.P. Hammett J. Am. Chem. Soc. 59 1937 96 103
31. A. Williams Free Energy Relationships in Organic and Bio-organic Chemistry 2003 Royal Chemical Cambridge chapters 1 and 2
32. C. Hansch, A. Leo, and R.W. Taft Chem. Rev. 91 1991 165 195
33. H. Vilter Phytochemistry 23 1984 1387 1390
34. M. Weyand, H.-J. Hecht, M. Kieß, M.-F. Liaud, H. Vilter, and D. Schomburg J. Mol. Biol. 293 1999 595 611
35. J. Hartung, O. Brücher, D. Hach, H. Schulz, H. Vilter, and G. Ruick Phytochemistry 69 2008 2826 2830
36. F. Björkstén Eur. J. Biochem. 5 1968 133 142
37. E. Verhaeghe, D. Buisson, E. Zekri, C. Leblanc, P. Potin, and Y. Ambroise Anal. Biochem. 379 2008 60 65
38. A.C. Jha, and B. Prasad J. Indian Chem. Soc. 57 1980 325 329
39. L. Gattermann, and T. Wieland Die Praxis des organischen Chemikers Vol. 43 1982 Walter de Gruyter Berlin chapter 3, p 230
40. D.W. Tischtschenko Chem. Zentralblatt 2 1928 767 768
41. S. Mabic, and J.-P. Lepoittevin Tetrahedron Lett. 36 1995 1705 1708
42. P. Suresh, S. Annalakshmi, and K. Pitchumani Tetrahedron 63 2007 4959 4967
43. Rogers, R.B.; Gerwick, B.C. US4642338 A1, 1987. CAS-RN: 2105-94-4.
44. J. Berthelot, C. Guette, P.-L. Desbène, J.-J. Basselier, P. Chaquin, and D. Masure Can. J. Chem. 67 1989 2061 2066
45. G. Bartoli, M. Bosco, R. Dalpozzo, E. Marcantoni, M. Massaccesi, and L. Sambri Eur. J. Org. Chem. 23 2003 4611 4617
46. O.S. Tee, and N.R. Iyengar J. Am. Chem. Soc. 107 1985 455 459
47. E. Berliner, and M.C. Beckett J. Am. Chem. Soc. 79 1957 1425 1431
48. O.S. Tee, and N.R. Iyengar Can. J. Chem. 65 1987 1714 1718
49. O.S. Tee, and N.R. Iyengar Can. J. Chem. 68 1990 1769 1773
50. V. Štěrba, O. Hrabík, J. Kaválek, J. Mindl, and A. Williams Org. Biomol. Chem. 1 2003 415 421
51. A. Gianguzza, C. De Stefano, A. Gianguzza, S. Sammartano, and P. Demianov Environ. Toxicol. Chem. 14 1995 767 774
52. I. Leupold, and H. Musso Justus Liebigs Ann. Chem. 746 1971 134 148
53. N.V. Shorina, D.S. Kosyakov, and K.G. Bogolitsyn Russ. J. Appl. Chem. 78 2005 125 129
54. W.L. Mock, and L.A. Morsch Tetrahedron 57 2001 2957 2964
55. D. Stefanidis, S. Cho, S. Dhe-Paganon, and W. Jencks J. Am. Chem. Soc. 115 1993 1650 1656
56. G. Guo, and F. Lin J. Hazard. Mater. 170 2009 645 653
57. O.S. Tee, M. Paventi, and J.M. Bennett J. Am. Chem. Soc. 111 1989 2233 2240
58. H.C. Brown, and Y. Okamoto J. Am. Chem. Soc. 80 1958 4979 4987
59. 2, see: G.A. Olah Acc. Chem. Res. 4 1971 240 248
60. V. Prakash Reddy, and G.K. Surya Prakash Z. Rappoport, Electrophilic Reactions of Phenols, The Chemistry of Phenols 2003 John Wiley Chichester, UK chapter 9, pp. 605-660
61. W.L.F. Armarego, and D.D. Perrin Purification of Laboratory Chemicals 4nd ed. 1996 Butterworth Heinemann Oxford
62. H. Weyl E. Müller, Methoden der organischen Chemie, Band V/4 Halogenverbindungen Vol. 4 1960 Georg Thieme Stuttgart 21 22 p 137
63. A.W. Francis J. Am. Chem. Soc. 47 1925 2340 2348
64. Y. Okada, M. Yokozawa, M. Akiba, K. Oishi, K. O-kawa, T. Akeboshi, Y. Kawamura, S. Inokuma, Y. Nakamura, and J. Nishimura Org. Biomol. Chem. 1 2003 2506 2511