Regioselective hydroxylation of phenols by simultaneous photochemical generation of phenol cation-radical and hydroxyl radical

Tetrahedron

Volumn 62, Issue 12, 2006, Pages 2927-2935

  Collado, Daniel ^a   Perez Inestrosa, Ezequiel ^a   Suau, Rafael ^a   Navarrete, Juan T Lopez ^a  

^a UNIVERSITY OF MÁLAGA   (Spain)

Author keywords

Photochemical electron transfer; Radical aromatic hydroxylation

Indexed keywords

HYDROXYL RADICAL; ISOQUINOLINE; PHENOL DERIVATIVE;

ARTICLE; CATION TRANSPORT; ELECTRON TRANSPORT; FLUORESCENCE SPECTROSCOPY; HYDROXYLATION; LUMINESCENCE; PHOTOCHEMISTRY; PHOTOLYSIS; PRIORITY JOURNAL; PROTON TRANSPORT; RADICAL REACTION;

EID: 32844458549     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.01.003     Document Type: Article

References (46)

1. W.H. Koppenol Redox Rep. 6 2001 229 234
2. K.D. Welch, T.Z. Davis, and S.D. Aust Arch. Biochem. Biophys. 397 2002 360 369
3. P.F. Fitzpatrick Annu. Rev. Biochem. 68 1999 355 381
4. V. Massey J. Biol. Chem. 269 1994 22459 22462
5. F.P. Guengerich Chem. Res. Toxicol. 14 2001 611 650
6. C.M. Bathelt, L. Ridder, A.J. Mulholland, and J.N. Harvey Org. Biomol. Chem. 2 2004 2998 3005
7. C.M. Bathelt, R.D. Schmid, and J. Pleiss J. Mol. Model. 8 2002 327 335
8. R.E. White, M.B. McCarthy, and K.D. Egeberg Arch. Biochem. Biophys. 228 1984 493 502
9. D.F.V. Lewis Pharmacogenomics 4 2003 387 395
10. D.F.V. Lewis, and J.M. Pratt Drug Metab. Rev. 30 1998 739 786
11. D. Davydov, T.M. Makris, V. Kofman, D.E. Werst, S.G. Sligar, and B.M. Hoffman J. Am. Chem. Soc. 123 2001 1403 1415
12. M.J. de Groot, R.W.A. Havenith, H.M. Vinkers, R. Zwaams, N.P.E. Vermeulen, and J.H. van Lenthe J. Comput. Aided Mol. Des. 12 1998 183 193
13. I. Schlichting, J. Berenzen, and K. Chu Science 287 2000 1615 1622
14. D. Harman Proc. Natl. Acad. Sci. U.S.A. 78 1981 7124 7128
15. T. Ozawa Physiol. Rev. 77 1997 425 464
16. K.B. Beckman, and B.N. Ames Physiol. Rev. 78 1998 547 581
17. H. Kaur, and B. Halliwell Anal. Biochem. 220 1994 11 15
18. D. Collado, E. Pérez-Inestrosa, and R. Suau J. Org. Chem. 68 2003 3574 3584
19. a of tyrosine changes from 10 to -2 upon oxidation (electron release), so the loss of the electron must be accompanied by deprotonation. In nature, the protein controls the reactivity of tyrosine and its radical by modulating the proton transfer reactions that are coupled with electron transfer: (a) P. Faller, C. Goussias, A.W. Rutherford, and S. Un Proc. Natl. Acad. Sci. U.S.A. 100 2003 8732 8735
20. J.A. Stubbe, and W.A. van der Donk Chem. Rev. 98 1998 705 762
21. F.G. Bordwell, and J.-P. Cheng J. Am. Chem. Soc. 113 1991 1736 1743
22. R. Hermann, S. Naumov, G.R. Mahalaxmi, and O. Brede Chem. Phys. Lett. 324 2000 265 272
23. M.R. Ganapathi, R. Hermann, S. Naumov, and O. Brede Phys. Chem. Chem. Phys. 2 2000 4947 4955
24. R. Hermann, S. Naumov, and O. Brede THEOCHEM 532 2000 69 80
25. O. Brede, R. Mehnert, and W. Naumann Chem. Phys. 115 1987 279 290
26. D.M. Guldi, and K.D. Asmus J. Am. Chem. Soc. 119 1997 5744 5745
27. M. Yi, and S. Scheiner Chem. Phys. Lett. 262 1996 567 572
28. W.T. Dixon, and D. Murphy J. Chem. Soc., Faraday Trans. 2 72 1976 1221 1230
29. F.G. Bordwell, and J.P. Cheng J. Am. Chem. Soc. 113 1991 1736 1743
30. Y.-R. Luo Handbook of Bond Dissociation Energies in Organic Compounds 2003 CRC Boca Raton, FL
31. S. Nagaoka, A. Kuranaka, H. Tsuboi, U. Hagashima, and K. Mukai J. Phys. Chem. 96 1992 2754 2761
32. A. Gilbert J. Baggott Essentials of Molecular Photochemistry 1991 Blackwell Oxford, UK
33. A.H. Said, F.M. Mhalla, C. Amatore, and J.-N. Verpeaux J. Electroanal. Chem. 464 1999 85 92
34. (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratman, R. E.; Burant, S.; Dapprich, J. M., Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, G.; Petersson, A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, I.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Manayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.1; Gaussian, Inc.: Pittsburgh, PA, 1998.
35. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
36. Y. Quin, and R.A. Wheeler J. Phys. Chem. 100 1996 10554 10563
37. W.J. Pietro, M.M. Francl, W.J. Hehre, D.J. Defrees, J.A. Pople, and J.S. Binkley J. Am. Chem. Soc. 104 1982 5039 5048
38. R. Joshi, S. Naumov, S. Kapoor, T. Mukherjee, R. Hermann, and O. Brede J. Phys. Org. Chem. 17 2004 665 674
39. O. Brede, S. Kapoor, T. Mukherjee, R. Hermann, and S. Naumov Phys. Chem. Chem. Phys. 4 2002 5096 5104
40. G.R. Dey, R. Hermann, S. Naumov, and O. Brede Chem. Phys. Lett. 310 1999 137 144
41. W.J. Dale, and H.E. Hennis J. Am. Chem. Soc. 78 1956 2543 2547
42. V. Levacher, and C. Moberg React. Polym. 24 1995 183 193
43. H.W. Gibson, and F.D. Popp J. Chem. Soc. (C) 1966 1860 1864
44. J.A. Carr, and K.S. Bisht Org. Lett. 6 2004 3297 3300
45. D. Collado, E. Pérez-Inestrosa, R. Suau, J.-P. Desvergne, and H. Bouas-Laurent Org. Lett. 4 2002 855 858
46. H. Kawai, Y. Kotake, and S. Ohta Chem. Res. Toxicol. 13 2000 1294 1301