Visible-light induced solvent-free photooxygenations of organic substrates by using [60]fullerene-linked silica gels as heterogeneous catalysts and as solid-phase reaction fields

Tetrahedron Letters

Volumn 47, Issue 9, 2006, Pages 1429-1432

  Hino, Tetsuo ^a   Anzai, Takahiro ^a   Kuramoto, Noriyuki ^a  

^a YAMAGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FULLERENE; PHENOL; SILICA GEL; SULFIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DIELS ALDER REACTION; ENE REACTION; IRRADIATION; PHOTOOXIDATION; SOLID STATE;

BETULACEAE;

EID: 31444453236     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.12.081     Document Type: Article

References (28)

1. P.T. Anastas, and J.C. Warner Green Chemistry. Theory and Practice 1998 Oxford University Press
2. E.L. Clennan, and A. Pace Tetrahedron 61 2005 6665
3. A.A. Frimer Singlet Oxygen Vol. I 1985 CRC Press Boca Raton
4. 2 Polymers and Biomolecules Vol. IV 1985 CRC Press Boca Raton, FL 36
5. K.M. Kadish R.S. Ruoff Fullerenes: Chemistry, Physics, and Technology 2000 John Wiley and Sons New York
6. Y. Takaguchi, Y. Yanagimoto, S. Fujima, and S. Tsuboi Chem. Lett. 33 2004 1142
7. J.L. Anderson, Y.-Z. An, Y. Rubin, and C.S. Foote J. Am. Chem. Soc. 116 1994 9763
8. M. Orfanopoulos, and S. Kambourakis Tetrahedron Lett. 35 1994 1945
9. H. Tokumaru, and E. Nakamura J. Org. Chem. 59 1994 1135
10. J.W. Aborgast, A.P. Darmanyan, C.S. Foote, Y. Rubin, F.N. Diederich, M.M. Alvarez, S.J. Anz, and R.L. Whetten J. Phys. Chem. 95 1991 11
11. J.W. Arbogast, and C.S. Foote J. Am. Chem. Soc. 113 1991 8886
12. R.R. Hung, and J.J. Grabowski J. Phys. Chem. 95 1991 6073
13. E.C. Blossey, D.C. Neckers, A.L. Thayer, and A.P. Schaap J. Am. Chem. Soc. 95 1973 5820
14. D. Madhavan, and K. Pitchumani Tetrahedron 57 2001 8391
15. N. Soggiu, H. Cardy, J.L.H. Jiwan, I. Leray, J.P. Soumillon, and S. Lacombe J. Photochem. Photobiol. 124 1999 1
16. X. Li, and V. Ramamurthy Tetrahedron Lett. 37 1996 5235
17. W. Zhou, and E.L. Clennan J. Am. Chem. Soc. 121 1999 2915
18. D. Latassa, O. Enger, C. Thilgen, T. Habicher, H. Offermanns, and F. Diederich J. Mater. Chem. 12 2002 1993
19. ® DAP beads (0.2-0.5 mm), namely a silicon polymer). On the other hand, the present catalyst prepared by linking of fullerene to amino-functionalized silica gels (40-60 μm), is able to be carried out in solvent-free photooxygenation by efficient utilization of silica gel part as a 'solid-phase reaction field'.
20. A.W. Jensen, and C. Daniels J. Org. Chem. 68 2003 207
21. T. Nagano, K. Arakane, A. Ryu, T. Masunaga, K. Shinmoto, S. Mashioko, and M. Hirobe Chem. Pharm. Bull. 42 1994 2291
22. K. Tanaka, and F. Toda Chem. Rev. 100 2000 1025
23. A.G. Griesbeck, and T.T. El-Idreesy Photochem. Photobiol. Sci. 4 2005 205
24. Fullerene (100 mg) and 3-aminopropyl-functionalized silica gel or 3-(diethylenetriamino)propyl-functionalized silica gel (500 mg, Aldrich Co. Ltd.) were reacted in toluene (50 mL) at 60°C for 8 h under Ar atmosphere. The resulting compound was filtrated, and then washed by hot toluene until the color of the toluene passing through the filter was clear to give the corresponding catalyst.
25. 3, and then the catalyst (100 mg) was added to the solution. The mixture was similarly irradiated in a quartz cell with visible-light (λ >380 nm), where air was passed through it continuously by using a bubbling system. After the reaction, the reaction mixture was filtrated and the catalyst was washed well with chloroform or ethyl acetate. Then, the resulting filtrate was concentrated under reduced pressure to afford the corresponding product.
26. R. Higgins, C.S. Foote, and H. Cheng Adv. Chem. Ser. 77 1968 102
27. J.H. Courtneidge, M. Bush, and L.-S. Loh J. Chem. Soc., Perkin Trans. 1 1992 1539
28. G. Ohloff, E. Klein, and G.O. Schenck Angew. Chem. 16 1961 578