B. Dutta et al. / Applied Catalysis A: General 382 (2010) 90–98
97
oxidation of ketones using molecular oxygen and sacrificial ben-
zaldehyde [78]. Recently, Steffen et al. reported the alumina
gen peroxide as oxidant [79]. Sever and Root proposed that the
ketone substrate and the hydrogen peroxide oxidant both interact
with the metal active site; thus Sn(IV) − H2O2 directly participates
in the addition reaction between hydrogen peroxide and acetone
[80].
[5] H. Heaney, in: S.D. Burke, R.L. Danheiser (Eds.), Handbook of Reagents for
Organic Synthesis—Oxidizing and Reducing Agents, Wiley, 1999, pp. 84–89.
[6] G.-J. Ten Brink, I.W.C.E. Arends, R.A. Sheldon, Chem. Rev. 104 (2004) 4105–4124.
[7] C. Jiménez-Sanchidrián, J.R. Ruiz, Tetrahedron 64 (2008) 2011–2026.
[8] G. Strukul, A. Varagnolo, F. Pinna, J. Mol. Catal. A 117 (1997) 413–423.
[9] C. Palazzi, F. Pinna, G. Strukul, J. Mol. Catal. A 151 (2000) 245–252.
[10] R. Bernini, E. Mincione, M. Cortese, R. Saladino, G. Gualandi, M.C. Belfiore, Tetra-
hedron Lett. 44 (2003) 4823–4825.
[11] J. Fischer, W.F. Holderich, Appl. Catal. A 180 (1999) 435–443.
[12] A. Berkessel, R.M.M. Andrae, Tetrahedron Lett. 42 (2001) 2293–2295.
[13] W. Hoelderich, J. Fischer, G. Schindler, P. Arntz, German Patent DE 19745442
(1999).
Leaching of the metal is a common problem in reactions in
the liquid phase (particularly in those involving oxidation with
peroxide by an effect of the chelating and solvolytic proper-
ties of the oxidant and products) [7,81]. Although no evidence
of metal leaching during the Baeyer–Villiger reaction appears
to exist, mesoporous catalysts containing titanium have been
found to release some metal during the oxidation of alcohols
with hydrogen peroxide; with tert-butylhydroperoxide as oxi-
dant, however, the amount of titanium leached was minimal
[81]. To test if the tin is leaching out from the catalyst dur-
ing reaction, the reaction mixture was filtered out hot after the
reaction is over and was subjected to atomic absorption spectro-
scopic analysis. The analyses show tin was absent in the filtrate.
Besides, the filtered mixture did not show any catalytic activ-
ity toward oxidation reactions. Therefore, it is clear that tin is
not leaching out from the catalyst during Baeyer–Villiger oxi-
dations. The Sn(salen)-NaY catalyst has been recovered from
the reaction mixture and has been reused successively three
times under the same reaction conditions. The solid catalyst has
been recovered by filtration after each reaction and has been
washed thoroughly with 1,4-dioxane. The recovered catalyst is
found to exhibit almost the same catalytic activity for cyclo-
hexanone oxidation reaction by tert-BuOOH in every run: first
run, cyclohexanone conversion = 75%, turnover = 1210; second run,
cyclohexanone conversion = 74%, turnover = 1215; third run, cyclo-
hexanone conversion = 75%, turnover = 1208. No induction period
was observed in any of the reactions (Fig. 6).
[14] B. Notari, Adv. Catal. 41 (1996) 253–334.
[15] K. Kaneda, S. Ueno, T. Imanaka, J. Mol. Catal. A 102 (1995) 135–138.
[16] U.R. Pillai, E. Sahle-Demessie, J. Mol. Catal. A: Chem. 191 (2003) 93–100.
[17] C. Li, J. Wang, Z. Yang, Z. Hu, Z. Lei, Catal. Commun. 8 (2007) 1202–1208.
[18] Q. Zhang, S. Wen, Z. Lei, React. Funct. Polym. 66 (2006) 1278–1283.
[19] C.-L. Li, Z.-W. Yang, S. Wu, Z.-Q. Lei, React. Funct. Polym. 67 (2007) 53–59.
[20] Z. Lei, Q. Zhang, J. Luo, X. He, Tetrahedron Lett. 46 (2005) 3505–3508.
[21] Z. Lei, Q. Zhang, R. Wang, G. Ma, C. Jia, J. Organomet. Chem. 691 (2006)
5767–5773.
[22] Z. Lei, G. Ma, C. Jian, Catal. Commun. 8 (2007) 305–309.
[23] A. Corma, L.T. Nemeth, M. Renz, S. Valencia, Nature 412 (2001) 423–425.
[24] M. Renz, T. Blasco, A. Corma, V. Fornés, R. Jensen, L. Nemeth, Chem. Eur. J. 8
(2002) 4708–4717.
[25] A. Corma, M.T. Navarro, M. Renz, J. Catal. 219 (2003) 242–246.
[26] A. Corma, V. Fornés, S. Iborra, M. Mifsud, M. Renz, J. Catal. 221 (2004) 67–76.
[27] A. Corma, S. Iborra, M. Mifsud, M. Renz, M. Susarte, Adv. Synth. Catal. 346 (2004)
257–262.
[28] M. Boronat, P. Concepción, A. Corma, M. Renz, S. Valencia, J. Catal. 234 (2005)
111–118.
[29] A. Corma, S. Iborra, M. Mifsud, M. Renz, J. Catal. 234 (2005) 96–100.
[30] M. Boronat, P. Concepción, A. Corma, M. Renz, Catal. Today 121 (2007) 39–44.
[31] A. Corma, S. Iborra, M. Mifsud, M. Renz, Arkivoc 9 (2005) 124–132.
[32] M. Boronat, A. Corma, M. Renz, G. Sastre, P.M. Viruela, Chem. Eur. J. 11 (2005)
6905–6915.
[33] J.-M. Brégeault, Dalton Trans. (2003) 3289–3302.
[34] W. Zhang, J.L. Loebach, S.R. Wilson, E.N. Jacobsen, J. Am. Chem. Soc. 112 (1990)
2801–2803.
[35] E.N. Jacobsen, Acc. Chem. Res. 33 (2000) 421–431.
[36] E.N. Jacobsen, in: I. Ojima (Ed.), Catalytic AsymmetricSynthesis, VCHPublishers,
New York, 1993, pp. 159–202.
[37] T. Katsuki, Coord. Chem. Rev. 140 (1995) 189–214.
[38] T. Uchida, R. Irie, T. Katsuki, Tetrahedron 56 (2000) 3501–3509.
[39] C. Adhikary, R. Bera, B. Dutta, S. Jana, G. Bocelli, A. Cantoni, S. Chaudhuri, S.
Koner, Polyhedron 27 (2008) 1556–1562.
[40] T. Niimi, T. Uchida, R. Irie, T. Katsuki, Adv. Synth. Catal. 1 (2001) 79–88.
[41] K.C. Gupta, A.K. Sutar, Coord. Chem. Rev. 252 (2008) 1420–1450.
[42] S. Koner, Chem. Commun. (1998) 593–594.
4. Conclusion
[43] P.K. Saha, B. Dutta, S. Jana, R. Bera, S. Koner, Polyhedron 26 (2006) 563–571.
[44] M. Pereyre, J.-P. Quintard, A. Rahm, Tin in Organic Synthesis, Butterworth, Lon-
don, 1987 (Chapter 4).
In summary, we have succeeded in immobilizing tin-salen moi-
ety into NaY zeolite matrix through an in situ synthesis procedure.
The complex undergoes noticeable distortion after immobilization
and remained in an octahedral geometry. The resulting material
was successfully employed in Baeyer–Villiger oxidation reactions
using tert-BuOOH as oxidant. The catalyst showed remarkable
activity, selectivity and high TON in Baeyer–Villiger oxidation reac-
tions. Since such reactions are industrially important, the catalyst
has some potential for commercial use.
[45] T. Hashiyama, Med. Res. Rev. 20 (2000) 485–501.
[46] T. Mukaiyama, S. Kobayashi, in: B.M. Trost (Ed.), Stereocontrolled Organic Syn-
thesis, Blackwell Scientific Publications, Oxford, 1994, pp. 37–65.
[47] J. Harada, A. Kimura, S. Tagami, J.P. Watanabe, Idemitsu Kosan Co., Ltd., Japan,
Patent Application, Japan, Kokai (1976).
[48] J.F. Larrow, US Patent, 6448449, B2, 66 (2002).
[49] Y.N. Belokon, A.A. Petrosyan, V.I. Maleev, T.F. Saveleva, A.V. Grachev, N.S. Ikon-
nikov, A.S. Sagiyan, Russ. Chem. Bull. 51 (2002) 2086–2089.
[50] A.A. Kelkar, S.S. Tonde, S.S. Divekar, R.V. Chaudhari, Council of Scientific and
Industrial Research, India, US Patent Application, U.S. Pat. Appl. Publ. (2002).
[51] A. Corma, M.T. Navarro, L. Nemeth, M. Renz, Chem. Commun. (2001)
2190–2191.
[52] R.H. Holm, G.W. Everett, A. Chakravorty, Prog. Inorg. Chem. 7 (1965) 83–214.
[53] A. Van den Bergen, R.J. Cozens, K.S. Murray, J. Chem. Soc. A (1970) 3060–3064.
[54] F. Bedioui, Coord. Chem. Rev. 144 (1995) 39–68 (and references therein).
[55] B. Dutta, S. Jana, R. Bera, P.K. Saha, S. Koner, Appl. Catal. A: Gen. 318 (2007)
89–94.
Acknowledgements
Financial support from the Ministry of Environment and Forests,
Government of India, by a grant (No. 19-5/2005-RE) (to SK) is
gratefully acknowledged. We also acknowledge the Department of
Science and Technology (DST), Government of India, for providing
funds to procure a Gas Chromatograph. BD thanks UGC and SJ (SRF)
thanks CSIR for a research fellowship. This work was also partly
supported by the grant for Strategic Research Project-2006 (No.
W18016) of Yokohama City University, Japan. We are grateful to
the referees for valuable suggestions.
[56] N. Herron, Inorg. Chem. 25 (1986) 4714–4717.
[57] R.M. Silverstein, G.C. Bassler, Spectrometric Identification of Organic Com-
pounds, John Wiley and Sons Inc., New York, 1963, pp. 55–56.
[58] D.K. Dey, M.K. Das, H. Nöth, Z. Naturforsch. 54b (1999) 145–154.
[59] R.M. Barrer, Hydrothermal Chemistry of Zeolite, Academic Press, New York,
1982.
[60] R. Ganesan, B. Viswanathan, J. Phys. Chem. B 108 (2004) 7102–7114.
[61] N.N. Greenwood, J.N.R. Ruddick, J. Chem. Soc. A (1967) 1679–1683.
[62] J. Phillip, M.S. Mullins, C. Curran, Inorg. Chem. 7 (1968) 1895–1898.
[63] H.A. Stockler, H. Sano, R.H. Herber, J. Chem. Phys. 45 (1966) 1182–1189.
[64] R.V. Parish, R.H. Platt, J. Chem. Soc. A (1969) 2145–2150.
[65] D.V. Naik, C. Curran, Inorg. Chem. 10 (1971) 1017–1020.
[66] B.W. Fitzsimmons, N.J. Seeley, A.W. Smith, J. Chem. Soc. A (1969) 143–146.
[67] R.K. Harris, S.T. Lawrence, S. Oh, V.G. Kumar Das, J. Mol. Struct. 347 (1995)
309–320.
References
[1] A. Baeyer, V. Villiger, Ber. Dtsch. Chem. Ges. 32 (1899) 3625–3627.
[2] G.C. Krow, Org. React. 43 (1993) 251–798.
[3] C.H. Hassall, Org. React. 9 (1957) 73–106.
[68] H. Jing, S.K. Edulji, J.M. Gibbs, C.L. Stern, H. Zhou, S-B.T. Nguyen, Inorg. Chem.
43 (2004) 4315–4327.
[4] C. Bolm, Adv. Catal. Process. 2 (1997) 43–68.