Abstract
A Mo(VI) complex, [MoO2HL(HOCH3)], HL = 2-[(2-hydroxy-benzylidene)-amino]-3-(4-hydroxy-phenyl)-propionic acid, was reacted with 3-(chloropropyl)-trimethoxysilane-functionalized silica that had been fused with magnetite to yield a magnetically separable catalyst in which the Mo complex was covalently linked to the silica matrix through a silane linkage. Both the free [MoO2HL(HOCH3)] and the immobilized complex function as efficient catalysts for the oxidation of olefins in the presence of tert-butylhydroperoxide as primary oxidant. The Fe3O4@SiO2/[MoO2L(HOCH3)] showed lower catalytic activity and turnover numbers compared to its homogeneous counterpart. However, the immobilized catalyst could be readily recovered from the reaction mixture by using a magnet and could be reused up to seven times without any loss of activity.
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Maurya MR (2012) Curr Org Chem 16:73–88
Bagherzadeh M, Tahsini L, Latifi R, Woo LK (2009) Inorg Chim Acta 362:3698–3702
Javadi MM, Moghadam M, Mohammadpoor-Baltork I, Tangestaninejad S, Mirkhani V, Kargar H, Nawaz Tahir M (2014) Polyhedron 72:19–26
Kuhn FE, Santos AM, Abrantes M (2006) Chem Rev 106:2455–2475
Ghorbanloo M, Ghamari S, Shahbakhsh N, Ng SW (2014) J Braz Chem Soc 25:2073–2079
Clark JH (1994) Supported reagents in organic reactions. VCH, Weinheim
Amini M, Mehdi Haghdoost M, Bagherzadeh M (2013) Coord. Chem Rev 257:1093–1121
Klencsar Z (2013) Hyperfine Interact 217:117–126
Heinert D, Martell AE (1962) J Am Chem Soc 84:3257–3263
Bagherzadeh M, Zare M, Amani V, Ellern A, Keith Woo L (2013) Polyhedron 53:223–229
Wang J, Zheng S, Shao Y, Liu J, Xu Z, Zhu D (2010) J Colloid Interface Sci 349:293–299
Deng YH, Wang CC, Hu JH, Yang WL, Fu SK (2005) Colloid Surf A 262:87–93
Saeedi MS, Tangestaninejad S, Moghadam M, Mirkhani V, Mohammadpoor-Baltork I, Khosropour AR (2013) Polyhedron 49:158–166
Nakamoto K (1986) Infrared and raman spectra of inorganic and coordination compounds. Wiley, New York
Topich J (1981) Inorg Chem 20:3704–3707
Zhang X, Niu H, Pan Y, Shi Y, Cai Y (2011) J Colloid Interface Sci 362:107–112
De Grave E, Persoons RM, Vanderberghe RE, Bakker PMA (1993) Phys Rev B 47:5881
Goya GF, Berquo TS, Fonseca FC, Morales MP (2003) J Appl Phys 94:3520–3527
Parida KM, Sahoo M, Singha S (2010) J Catal 276:161–169
Maiti SK, Dinda S, Gharah N, Bhattacharyya R (2006) New J Chem 30:479–489
Zhang Y, Zhen L, Sun W, Xia C (2008) Catal Commun 10:237–242
Fernandes CI, Carvalho MD, Ferreira LP, Nunes CD, Vaz PD (2014) J Organomet Chem 760:2–10
Li Y, Fu X, Gong B, Zou X, Tu X, Chen J (2010) J Mol Catal A: Chem 322:55–62
Sheldon RA (1973) Vav Doorn JA. J Catal 31:427–437
Masteri-Farahani M, Farzaneh F, Ghandi M (2006) J Mol Catal A: Chem 248:53–60
Deng Y, Cai Y, Sun Z, Liu J, Liu C, Wei J, Li W, Liu C, Wang Y, Zhao D (2010) J Am Chem Soc 132:8466–8473
Grivani G, Tangestaninejad S, Halili A (2007) Inorg Chem Commun 10:914–917
Kuhn FE, Groarke M, Bencze E, Herdtweck E, Prazeres A, Santos AM, Calhorda MJ, Romao CC, Lopes AD, Pillinger M, Goncalves IS (2002) Chem Eur J 8:2370–2383
Choudhary VR, Jha R, Jana P (2008) Catal Commun 10:205–207
Mohammadikish M, Masteri-Farahani M, Mahdavi S (2014) J Magn Magn Mater 354:317–323
Silva NU, Fernandes CI, Nunes TG, Saraivaa MS, Nunes Cd, Vaz PD (2011) Appl Catal A 408:105–116
Moradi-Shoeili Z, Boghaei DM, Amini M, Bagherzadeh M, Notash B (2013) Inorg Chem Commun 27:26–30
Rayati S, Rafiee N, Wojtczak A (2012) Inorg Chim Acta 386:27–35
Shylesh S, Schweizer J, Demeshko S, Schunemann V, Ernst S, Thiel WR (2009) Adv Synth Catal 351:1789–1795
Nakayama N, Tsuchiya S, Ogawa S (2007) J Mol Catal A 277:61–71
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Authors are thankful to University of Zanjan for financial support of this study.
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Ghorbanloo, M., Mohamadi, A., Amini, M. et al. Use of a molybdenum(VI) dioxide complex as a homogeneous and heterogeneous magnetically recoverable epoxidation catalyst. Transition Met Chem 40, 321–331 (2015). https://doi.org/10.1007/s11243-015-9920-7
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DOI: https://doi.org/10.1007/s11243-015-9920-7