An Efficient, Catalytic, Aerobic, Oxidative Iodination of Arenes Using the H5PV2Mo10O40 Polyoxometalate as Catalyst

Journal of Organic Chemistry

Volumn 68, Issue 24, 2003, Pages 9510-9512

  Branytska, Olena V ^a   Neumann, Ronny ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

WASTE-FREE METHODS;

CATALYSTS; IODINE; OXIDATION; OXYGEN;

ORGANIC COMPOUNDS;

1 BROMO 2 IODOBENZENE; 1 BROMO 4 IODOBENZENE; 1 CHLORO 2 IODOBENZENE; 1 CHLORO 4 IODOBENZENE; 1 IODO 2 METHOXYNAPHTHALENE; 1 IODONAPHTHALENE; 2 IODO 1,3 DIMETHOXYBENZENE; 2 IODO 1,3,5 TRIMETHYLBENZENE; 2 IODO 1,4 DIMETHOXYBENZENE; 2 IODO 1,4 DIMETHYLBENZENE; 2 IODO 4 METHYLANISOLE; 2 IODOANILINE; 2 IODOBENZOTHIOPHENE; 2 IODOPHENOL; 2 IODOTHIOPHENE; 2 IODOTOLUENE; 3 IODOBENZOTHIOPHENE; 4 IODO 1 METHOXYNAPHTHALENE; 4 IODO 1,2 DIMETHOXYBENZENE; 4 IODOANILINE; 4 IODOANISOLE; 4 IODODIPHENYL; 4 IODOPHENOL; 4 IODOTOLUENE; 4,4' DIIODOBIPHENYL; ANISOLE; IODINE; IODINE DERIVATIVE; OXYGEN; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; ATMOSPHERE; CATALYSIS; CATALYST; IODINATION; OXIDATION; PRODUCTIVITY; SYNTHESIS;

EID: 0344823659     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035271h     Document Type: Article

References (27)

1. Metal-Catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1997.
2. Merkushev, E. B. Synthesis 1988, 10, 923-937.
3. (a) Mattern, D. L. J. Org. Chem. 1984, 49, 3051-3053.
4. (b) Lulinski, P.; Skulski, L. Bull. Chem. Soc. Jpn. 2000, 73, 951-956.
5. (c) Suzuki, H.; Nakamura, K.; Goto, R. Bull. Chem. Soc. Jpn. 1966, 39, 128-131.
6. Brazdil, L. C.; Cutler, C. J. J. Org. Chem. 1996, 61, 9621-9622.
7. (a) Barnett, J. R.; Andrews, L. J.; Keefer, R. M. J. Am. Chem. Soc. 1972, 94, 6129-6134.
8. (b) Wing-Wah, Sy.; Lodge, B. A. Tetrahedron Lett. 1989, 30, 3769-3772.
9. Pagni, R. M.; Kabalka, G. W.; Boothe, R.; Gaetano, K.; Stewart, L. J.; Conaway, R.; Dial, C.; Gray, D.; Larson, S.; Luidhardt, T. J. Org. Chem. 1988, 53, 4477-4482.
10. Barluenga, J.; Gonzalez, J. M.; Garcia-Martin, M. A.; Campos, P. J.; Asensio, G. J. Org. Chem. 1993, 58, 2058-2060.
11. Krassowska-Swiebocka, B.; Lulinski, P.; Skulski, L. Synthesis 1995, 8, 926-928.
12. Merkushev, E. B.; Simakhina, N. D.; Koveshnikova, G. M. Synthesis 1980, 6, 486-487.
13. Asakura, J.; Robins, M. J. J. Org. Chem. 1990, 55, 4928-4933.
14. (a) Rozen, S.; Zamir, D. J. Org. Chem. 1990, 55, 3552-3555.
15. (b) Shellhamer, D. F.; Jones, B. C.; Pettus, B. J.; Petts, T. L.; Stringer, J. M.; Heasley, V. L. J. Fluorine Chem. 1998, 88, 37-39.
16. (a) Kosynkin, D. V.; Tour, J. M. Org. Lett. 2001, 3, 991-992.
17. (b) Kajigaeshi, S.; Kakinami, T.; Yamasaki, H.; Fujisaki, S.; Okamoto, T. Bull. Chem. Soc. Jpn. 1988, 61, 600-602.
18. (c) Kajigaeshi, S.; Kakinami, T.; Yamasaki, H.; Fujisaki, S.; Kondo, M.; Okamoto, T. Chem. Lett. 1987, 2109-2122.
19. (d) Custelceanu, R.; Vlassa, M.; Silberg, I. A. Monatsh. Chem. 1997, 128, 919-925.
20. (e) Hajipour, A. R.; Arbabian, M.; Ruoho, A. E. J. Org. Chem. 2002, 67, 8622-8624.
21. (f) Wariishi, K.; Morishima, S.-I.; Inagaki, Y. Org. Process Res. Dev. 2003, 7, 98-100.
22. (a) Kozhevnikov, I. V. Chem. Rev. 1998, 98, 171-198.
23. (b) Kozhevnikov, I. V. Catalysis by Polyoxometalates; Wiley: Chichester, England, 2002.
24. (c) Neumann, R. Prog. Inorg. Chem. 1998, 47, 317-370.
25. (d) Hill, C. L.; Prosser-McCartha, C. M. Coord. Chem. Rev. 1995, 143, 407-455.
26. (e) Okuhara, T.; Mizuno, N.; Misono, M. Adv. Catal. 1996, 41, 113-252.
27. Neumann, R.; Assael, I. J. Chem. Soc., Chem. Commun. 1988, 1285-1287.