Semiconductor-mediated oxidative dimerization of 1-naphthols with dioxygen and O-demethylation of the enol-ethers by SnO 2 without dioxygen

Tetrahedron

Volumn 60, Issue 47, 2004, Pages 10681-10693

  Takeya, Tetsuya ^a   Otsuka, Tsuyoshi ^a   Okamoto, Iwao ^a   Kotani, Eiichi ^a  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Binaphthol; Demethylation; Dioxygen; Oxidative coupling; Semiconductor

Indexed keywords

1 NAPHTHOL DERIVATIVE; CHARCOAL; ETHER DERIVATIVE; OXYGEN; TIN DERIVATIVE; TIN OXIDE; UNCLASSIFIED DRUG; ZIRCONIUM OXIDE;

ARTICLE; CATALYST; DEMETHYLATION; DIMERIZATION; IRRADIATION; OXIDATION; PRIORITY JOURNAL; SEMICONDUCTOR;

EID: 5644256973     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.09.003     Document Type: Article

References (72)

1. G. Bringmann, R. Walter, and R. Weirich Angew. Chem., Int. Ed. Engl. 29 1990 977 991
2. J.S. Swenton Acc. Chem. Res. 16 1983 74 81
3. (c) Progress in the Chemistry of Organic Natural Products; Herz, W., Falk, H., Kirby, G. W., Moore, R. E., Eds.; Springer: Wien, New York, 2001; Vol. 82, pp. 38-64.
4. A.I. Meyers, and J.J. Willemsen Tetrahedron 54 1998 10493 10511
5. Y. Kashiwagi, H. Ono, and T. Osa Chem. Lett. 1993 81 84
6. H.R. El-Seedi, S. Yamamura, and S. Nishiyama Tetrahedron Lett. 43 2002 3301 3304
7. H.R. El-Seedi, S. Yamamura, and S. Nishiyama Tetrahedron 58 2002 7485 7489
8. Y. Shizuri, K. Nakamura, and S. Yamamura J. Chem. Soc. Chem. Commun. 1985 530 531
9. B.D. Gates, P. Dalidowicz, A. Tebben, S. Wang, J. Swenton, and S J. Org. Chem. 57 1992 2135 2143
10. M.L. Kerns, S.M. Conroy, and J.S. Swenton Tetrahedron Lett. 35 1994 7529 7532
11. K. Chiba, M. Jinno, R. Kuramoto, and M. Tada Tetrahedron Lett. 39 1998 5527 5530
12. K. Chiba, T. Arakawa, and M. Tada J. Chem. Soc., Perkin Trans. 1 1998 2939 2942
13. K. Chiba, M. Fukuda, S. Kim, Y. Kitano, and M. Tada J. Org. Chem. 64 1999 7654 7656
14. J. Hassan, M. Sévignon, C. Gozzi, E. Schlz, and M. Lemarie Chem. Rev. 102 2002 1359 1469
15. G. Bringnmann, and S. Tasler Tetrahedron 57 2001 331 343
16. Y. Tanoue, K. Sakata, M. Hashimoto, S. Morishita, M. Hamada, N. Kai, and T. Nagai Tetrahedron 58 2002 99 104
17. B.C. Maiti, O.C. Musgrave, and D. Skoyles J. Chem. Soc., Chem. Commun. 1976 244 245
18. D.-R. Hwang, C.-P. Chen, and B.-J. Uang J. Chem. Soc., Chem. Commun. 1999 1207 1208
19. Z. Luo, Q. Liu, L. Gong, X. Cui, A. Mi, and Y. Jiang Angew. Chem., Int. Ed. 41 2002 4532 4535
20. V.B. Sharman, S.L. Jain, and J.B. Sain Tetrahedron Lett. 44 2003 2655 2656
21. A. Corma, and H. Garcia Chem. Rev. 102 2002 3837 3892
22. T.-S. Li, H.-Y. Duan, B.-Z. Li, B.-B. Tewari, and S.-H. Li J. Chem. Soc., Perkin Trans. 1 1999 291 293
23. T. Sakamoto, H. Yonehara, and C. Pac J. Org. Chem. 62 1997 3194 3199
24. F. Toda, K. Tanaka, and S. Iwata J. Org. Chem. 54 1989 3007 3009
25. D.H.R. Barton J. Mol. Catal. 117 1997 3 7
26. A. Maldotti, A. Molinari, and R. Amadelli Chem. Rev. 102 2002 3811 3836
27. M.R. Hoffmann, S.T. Martin, W. Choi, and D.W. Bahnemann Chem. Rev. 95 1995 69 96
28. A. Fujishima, and K. Honda Nature 238 1972 37 38
29. M.A. Fox Top. Curr. Chem. 142 1987 71 99
30. D.E. Bergbreiter Chem. Rev. 102 2002 3345 3384
31. M. Poliakoff, and P. Anastas Nature 413 2001 257 258
32. T. Ogata, I. Okamoto, E. Kotani, and T. Takeya Tetrahedron 60 2004 3941 3948
33. T. Takeya, H. Doi, T. Ogata, T. Otsuka, I. Okamoto, and E. Kotani Tetrahedron 60 2004 6295 6310
34. T. Otsuka, I. Okamoto, E. Kotani, and T. Takeya Tetrahedron Lett. 45 2004 2643 2647
35. T. Ogata, I. Okamoto, H. Doi, E. Kotani, and T. Takeya Tetrahedron Lett. 44 2003 2041 2044
36. T. Funabiki, H. Ohashi, T. Sugimoto, and S. Yoshida J. Mol. Catal. 69 1991 407 418
37. J.S. Calderon, and R.H. Thomson J. Chem. Soc., Perkin Trans. 1 1988 583 586
38. B.C. Maiti, and O.C. Musgrave J. Chem. Soc., Perkin Trans. 1 1986 675 681
39. A.V.B. Sankaram, V.V.N. Reddy, and G.S. Sidhu Phytochemistry 20 1981 1093 1096
40. M.A. Brimble, and T.J. Brenstrum J. Chem. Soc., Perkin Trans. 1 2001 1624 1634
41. G. Bringmann, R. Götz, P.A. Keller, R. Walter, M.R. Boyd, F. Lang, A. Garcia, J.J. Walsh, I. Tellitu, K.V. Bhaskar, and T.R. Kelly J. Org. Chem. 63 1998 1090 1097
42. 1H NMR spectra of NPOH 1a-c, the signal (δ 10.50 ppm) of a hydroxyl proton at the C1-position in 1b was observed at lower field than the corresponding signals (δ 5.66 and 5.32 ppm) in 1a and 1c.
43. P.V. Kamat Chem. Rev. 93 1999 267 300
44. K.U. Ingold Acc. Chem. Res. 2 1969 1 9
45. E.C. Horswill, and K.U. Ingold Can. J. Chem. 44 1966 263 277
46. N. Sergent, P. Gélin, L. P-Camby, H. Praliaud, and G. Thomas Phys. Chem. Chem. Phys. 4 2002 4802 4808
47. J. Zhuang, C.N. Rusu, and J.T. Yates Jr. J. Phys. Chem. B 103 1999 6957 6967
48. 1H shift correlation spectroscopy (C-H COSY), 1H-detected heteronuclear multiple bond connectivity (HMBC); and nuclear Overhauser enhancement and exchange spectroscopy (NOESY) experiments.
49. D. Boger B.M. Trost I. Fleming Comprehensive Organic Synthesis 1991 Pergamon Oxford 451 512 Vol. 5, Chapter 4.3
50. K.A. Jorgensen Angew. Chem., Int. Ed. 39 2000 3558 3588
51. L. Giraud, and A. Giraud Synthesis 1998 1153 1160
52. J. Nakayama J. Synth. Org. Chem. Jpn 61 2003 1106 1115
53. L.F. Tietze, T. Brumby, M. Pretor, and G. Remberg J. Org. Chem. 53 1988 810 820
54. C.C. Pye, J.D. Xidos, R.A. Poirier, and D.J. Burnell J. Phys. Chem. A 101 1997 3371 3376
55. R. Hoffmann, and R.B. Woodward J. Am. Chem. Soc. 87 1965 4388 4389
56. V. Nair, and S. Kumar Tetrahedron 52 1996 4029 4040
57. V. Nair, B. Mathew, K.V. Radhakrishnan, and N.P. Rath Tetrahedron 55 1999 11017 11026
58. V. Nair, and S. Kumar J. Chem. Soc., Perkin Trans. 1 1996 443 447
59. K.C. Nicolau, S.A. Snyder, T. Montagnon, and G. Vassilikogiannakis Angew. Chem., Int. Ed. 41 2002 1668 1698
60. A.G. Gonzalez, N.L. Alvarenga, A. E-Braun, A.G. Ravelo, I.L. Bazzocchi, and L. Moujir Tetrahedron 52 1996 9597 9608
61. O. Shirota, H. Morita, K. Takeya, and H. Itokawa Tetrahedron 51 1995 1107 1120
62. A.G. Gonzalez, N.L. Alvarenga, I.L. Bazzocchi, A.G. Ravelo, and L. Moujir J. Nat. Prod. 62 1999 1185 1187
63. S. Laschat Angew. Chem., Int. Ed. Engl. 35 1996 289 291
64. H. Oikawa, K. Yagi, K. Watanabe, M. Honma, and A. Ichikawa J. Chem. Soc., Chem. Commun. 1997 97 98
65. R.L. Hannan, R.B. Barber, and H. Rapoport J. Org. Chem. 44 1979 2153 2158
66. G. Wurm, and B. Goebler Arch. Pharm. 322 1989 569 572
67. T. Takeya, M. Kajiyama, C. Nakamura, and S. Tobinaga Chem. Pharm. Bull. 47 1999 209 219
68. C.P. Casey, C.R. Jones, and H. Tukada J. Org. Chem. 46 1981 2089 2092
69. C.P. Casey, C.R. Jones, and H. Tukada J. Org. Chem. 63 1998 1090 1097
70. H. Laatsch Liebigs Ann. Chem. 4 1980 1321 1347
71. A.G. González, N.L. Alvarenga, A. E-Braun, A.G. Ravelo, I.L. Bazzocchi, and L. Moujir Tetrahedron 52 1996 9597 9608
72. J.M. Saa, M. Jeronimo, and C. Rubido J. Org. Chem. 51 1986 4471 4473