Copyright (c) 2015 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Efficient Photooxygenation of Furans using Oxygen with Wool-Immobilizing Rose Bengal as Green Photosensitizer
Corresponding Author(s) : Yan Zhang
Asian Journal of Chemistry,
Vol. 27 No. 1 (2015): Vol 27 Issue 1
Abstract
A new type of solid-supported photosensitizer was prepared from Rose Bengal and wool via acid dye dyeing process. The wool-Rose-bengal photosensitizer was characterized by Fourier transform infrared spectrometer (FTIR), scanning electron microscope and fastness test. This sensitizer was used as heterogeneous photocatalyst to promote furans oxidation to the corresponding butenolides in excellent yields (90 %). The sensitizer could be easily recovered from the reaction mixture by filtration and reused in the new cycle of the reaction.
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References
J.H. Clark and D.J. Macquarrie, Handbook of Green Chemistry & Technology, Blackwell Science (2002).
M. Oelgemoller, N. Healy, L. de Oliveira, C. Jung and J. Mattay, Green Chem., 8, 831 (2006); doi:10.1039/b605906f.
(a) E.C. Blossey, D.C. Neckers, A.L. Thayer and A.P. Schaap, J. Am. Chem. Soc., 95, 5820 (1973); doi:10.1021/ja00798a094; (b) A.P. Schaap, A.L. Thayer, E.C. Blossey and D.C. Neckers, J. Am. Chem. Soc., 97, 3741 (1975); doi:10.1021/ja00846a030; (c) J. Paczkowski and D.C. Neckers, Macromolecules, 18, 1245 (1985); doi:10.1021/ma00148a035; (d) S.N. Gupta, S.M. Linden, A. Wrzyszczynski and D.C. Neckers, Macromolecules, 21, 51 (1988); doi:10.1021/ma00179a012; (e) A.P. Schaap, A.L. Thayer, K.A. Zaklika and P.C. Valenti, J. Am. Chem. Soc., 101, 4016 (1979); doi:10.1021/ja00508a076.
(a) S. Horsa, K. Perez and J. Miksovska, J. Photochem. Photobiol. Chem., 221, 84 (2011); doi:10.1016/j.jphotochem.2011.04.029; (b) C. Marisa, D.S. Ilaria, R. Marotta, A. Roberto and C. Vincenzo, J. Photochem. Photobiol. Chem., 210, 69 (2010); doi:10.1016/j.jphotochem.2009.12.003; (c) H. Xu, W.K. Chan and D.K.P. Ng, Synthesis, 1791 (2009); doi:10.1055/s-0028-1088066; (d) C. Niles, J.S. Wishnok and S.R. Tannenbaum, Org. Lett., 3, 963 (2001); (e) H.R. Li, L.Z. Wu and C.H. Tung, J. Am. Chem. Soc., 122, 2446 (2000); doi:10.1021/ja9917161; (f) S.M.A. Pinto, Â.C.B. Neves, M.J.F. Calvete, A.R. Abreu, M.T.S. Rosado, T. Costa, H.D. Burrows and M.M. Pereira, J. Photochem. Photobiol. Chem., 242, 59 (2012); doi:10.1016/j.jphotochem.2012.05.031;(g) P.K. Frederiksen, S.P. McIlroy, C.B. Nielsen, L. Nikolajsen, E. Skovsen, M. Jørgensen, K.V. Mikkelsen and P.R. Ogilby, J. Am. Chem. Soc., 127, 255 (2005); doi:10.1021/ja0452020; (h) C. Schweitzer, Z. Mehrdad, A. Noll, E.W. Grabner and R. Schmidt, J. Phys. Chem. A, 107, 2192 (2003); doi:10.1021/jp026189d; (i) S.G. DiMagno, P.H. Dussault and J.A. Schultz, J. Am. Chem. Soc., 118, 5312 (1996); doi:10.1021/ja960736p; (j) Talukdar, Y. Takaguchi, Y. Yanagimoto, S. Tsuboi, M. Ichihara and K. Ohta, Bull. Chem. Soc. Jpn., 79, 1983 (2006); doi:10.1246/bcsj.79.1983; (k) A.W. Jensen and C. Daniels, J. Org. Chem., 68, 207 (2003);doi:10.1021/jo025926z; (l) M. Ohno, N. Koide, H. Sato and S. Eguchi, Tetrahedron, 53, 9075 (1997); doi:10.1016/S0040-4020(97)00600-5.
(a) M.J. Moreno, E. Monson, R.G. Reddy, A. Rehemtulla, B.D. Ross, M. Philbert, R.J. Schneider and R. Kopelman, Sens. Actuators B, 90, 82 (2003); doi:10.1016/S0925-4005(03)00057-1; (b) W. Tang, H. Xu, R. Kopelman and M. A. Philbert, Photochem. Photobiol., 81, 242 (2005); doi:10.1562/2004-05-24-RA-176.1.
(a) A. Labib, V. Lenaerts, F. Chouinard, J.C. Leroux, R. Ouellet and J.E. van Lier, Pharm. Res., 8, 1027 (1991); doi:10.1023/A:1015809124895; (b) E. Allemann, J. Rousseau, N. Brasseur, V.S. Kudrevich, K. Lewis and J.E. van Lier, Int. J. Cancer, 66, 821 (1996); doi:10.1002/(SICI)1097-0215(19960611)66:6<821::AID-IJC19>3.0.CO;2-5.
(a) F. Yan and R. Kopelman, Photochem. Photobiol., 78, 587 (2003); doi:10.1562/0031-8655(2003)078<0587:TEOMIS>2.0.CO;2; (b) T.Y. Ohulchanskyy, I. Roy, L.N. Goswami, Y. Chen, E.J. Bergey, R.K. Pandey, A.R. Oseroff and P.N. Prasad, Nano Lett., 7, 2835 (2007); doi:10.1021/nl0714637; (c) S. Kim, T.Y. Ohulchanskyy, H.E. Pudavar, R.K. Pandey and P.N. Prasad, J. Am. Chem. Soc., 129, 2669 (2007); doi:10.1021/ja0680257.
M.S. Galletero, Chem. Phys. Lett., 370, 829 (2003); doi:10.1016/S0009-2614(03)00203-3.
M.I. Burguete, F. Galindo, R. Gavara, S.V. Luis, M. Moreno, P. Thomas and D.A. Russell, Photochem. Photobiol. Sci., 8, 37 (2009); doi:10.1039/b810921d; (b) M. Nowakowska, M. Kepczynski and M. Dabrowska, Macromol. Chem. Phys., 202, 1697 (2001); doi:10.1002/1521-3935(20010601)202:9<1679::AID-MACP1679>3.0.CO;2-R; (c) H. Koizumi, Y. Kimata, Y. Shiraishi and T. Hirai, Chem. Commun., 1846 (2007); doi:10.1039/b617718b; (d) M.I. Burguete, R. Gavara, F. Galindo and S.V. Luis, Tetrahedron Lett., 51, 3360 (2010); doi:10.1016/j.tetlet.2010.04.065; (e) F. Prat and C.S. Foote, Photochem. Photobiol., 67, 626 (1998); doi:10.1111/j.1751-1097.1998.tb09103.x.
(a) B.M. Trost and F.D. Toste, J. Am. Chem. Soc., 125, 3090 (2003); doi:10.1021/ja020988s; (b) L.S. Hegedus and L. Geisler, J. Org. Chem., 66, 1064 (2001); doi:10.1021/jo004039y; (c) P. de March, M. Figueredo, J. Font and J. Raya, Org. Lett., 2, 163 (2000); doi:10.1021/ol991261k.
Z. Yan, W. Wei, H. Xun and S. Anguo, Chem. Lett., 41, 1500 (2012); doi:10.1246/cl.2012.1500.
(a) M.I. Burguete, R. Gavara, F. Galindo and S.V. Luis, Catal. Commun., 11, 1081 (2010); doi:10.1016/j.catcom.2010.05.013; (b) A.M. Braun, H. Dahn, E. Gassmann, I. Gerothanassis, L. Jakob, J. Kateva, C.G. Martinez and E. Oliveros, Photochem. Photobiol., 70, 868 (1999); doi:10.1111/j.1751-1097.1999.tb08295.x.
K. Gollnick and K. Knutzen-Mies, J. Org. Chem., 56, 4017 (1991); doi:10.1021/jo00012a040.