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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 24
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Original Articles

Fe3O4 Nanoparticles as an Efficient and Magnetically Recoverable Catalyst for the Synthesis of α,β-Unsaturated Heterocyclic and Cyclic Ketones under Solvent-Free Conditions

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Pages 3357-3362 | Received 21 Jan 2013, Published online: 05 Sep 2013

REFERENCES

  • (a) Sun , S. ; Zeng , H. Size-controlled synthesis of magnetite nanoparticles . J. Am. Chem. Soc. 2002 , 124 , 8204 – 8205 ; (b) Latham , A. H. ; Williams , M. E. Controlling transport and chemical functionality of magnetic nanoparticles . Acc. Chem. Res. 2008 , 41 , 411 – 420 ; (c) Laurent , S. ; Forge , D. ; Port , M. ; Roch , A. ; Robic , C. ; Elst , L. V. ; Muller , R. N. Magnetic iron oxide nanoparticles: Synthesis, stabilization, vectorization, physicochemical characterizations, and biological applications . Chem. Rev. 2008 , 108 , 2064 – 2110 .
  • Guin , D. ; Baruwati , B. ; Manorama , S. V. Pd on amine-terminated ferrite nanoparticles: A complete magnetically recoverable facile catalyst for hydrogenation reactions . Org. Lett. 2007 , 9 , 1419 – 1421 .
  • (a) Polshettiwar , V. ; Baruwati , B. ; Varma , R. S. Magnetic nanoparticle-supported glutathione: A conceptually sustainable organocatalyst . Chem. Commun. 2009 , 1837 – 1839 ; (b) Polshettiwar , V. ; Baruwati , B. ; Varma , R. S. Nanoparticle-supported and magnetically recoverable nickel catalyst: A robust and economic hydrogenation and transfer hydrogenation protocol . Green Chem. 2009 , 11 , 127 – 131 ; (c) Zhang , D.-H. ; Li , G.-D. ; Lia , J.-X. ; Chen , J.-S. One-pot synthesis of Ag–Fe3O4 nanocomposite: A magnetically recyclable and efficient catalyst for epoxidation of styrene . Chem. Commun. 2008 , 3414 – 3416 ; (d) Polshettiwar , V. ; Varma , R. S. Nanoparticle-supported and magnetically recoverable ruthenium hydroxide catalyst: Efficient hydration of nitriles to amides in aqueous medium . Chem.—Eur. J. 2009 , 15 , 1582 – 1586 ; (e) Ge , J. ; Zhang , Q. ; Zhang , T. ; Yin , Y. Core–satellite nanocomposite catalysts protected by a porous silica shell: Controllable reactivity, high stability, and magnetic recyclability . Angew. Chem., Int. Ed. 2008 , 47 , 8924 – 8928 .
  • Mojtahedi , M. M. ; Abaee , M. S. ; Eghtedari , M. Superparamagnetic iron oxide as an efficient and recoverable catalyst for rapid and selective trimethylsilyl protection of hydroxyl groups . Appl. Organometal. Chem. 2008 , 22 , 529 – 532 .
  • Mojtahedi , M. M. ; Abaee , M. S. ; Alishiri , T. Supermagnetic iron oxide as an efficient catalyst for the one-pot, solvent-free synthesis of α-amino nitriles . Tetrahedron Lett. 2009 , 50 , 2322 – 2325 .
  • Lü , H.-Y. ; Yang , S.-H. ; Deng , J. ; Zhang , Z.-H. Magnetic Fe3O4 nanoparticles as new, efficient, and reusable catalysts for the synthesis of quinoxalines in water . Aus. J. Chem. 2010 , 63 , 1290 – 1296 .
  • Zeng , T. ; Chen , W.-W. ; Cirtiu , C. M. ; Moores , A. ; Song , G. ; Li , C.–J. Fe3O4 nanoparticles: A robust and magnetically recoverable catalyst for three-component coupling of aldehyde, alkyne, and amine. Green Chem. 2010, 12, 570–573.
  • Sreedhar , B. ; Suresh Kumar , A. ; Surendra Reddy , P. Magnetically separable Fe3O4 nanoparticles: An efficient catalyst for the synthesis of propargylamines . Tetrahedron Lett. 2010 , 51 , 1891 – 1895 .
  • Martinez , R. ; Ramon , D. J. ; Yus , M. Unmodified nano-powder magnetite catalyzes a four-component aza-Sakurai reaction . Adv. Synth. Catal. 2008 , 350 , 1235 – 1240 .
  • Martinez , R. ; Ramon , D. J. ; Yus , M. Selective N-monoalkylation of aromatic amines with benzylic alcohols by a hydrogen autotransfer process catalyzed by unmodified magnetite . Org Biomol. Chem. 2009 , 7 , 2176 – 2181 .
  • Zeng , T. ; Song , G. ; Moores , A. ; Li , C.-J. Magnetically recoverable iron nanoparticle–catalyzed cross-dehydrogenative coupling (CDC) between two Csp3-H bonds using molecular oxygen . Synlett 2010 , 2002 – 2008 .
  • Firouzabadi , H. ; Iranpoor , N. ; Gholinejad , M. ; Hoseini , J. Magnetite (Fe3O4) nanoparticles–catalyzed Sonogashira–Hagihara reactions in ethylene glycol under ligand-free conditions . Adv. Synth. Catal. 2011 , 353 , 125 – 132 .
  • Nasr-Esfahani , M. ; Hoseini , S. J. ; Mohammadi , F. Fe3O4 nanoparticles as an efficient and magnetically recoverable catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions . Chin. J. Catal. 2011 , 32 , 1484 – 1489 .
  • Zare , L. ; Nikpassand , M. Evaluation of nano-Fe3O4 as a green catalyst for the synthesis of mono-, bis-, and tris-diindolyl methanes . E-J. Chem. 2012 , 9 , 1623 – 1631 .
  • Kim , E. ; Kim , S. ; Kim , B. M. Efficient and chemoselective reduction of olefins catalyzed by Fe3O4 nanoparticles using hydrazine hydrate . Bull. Korean Chem. Soc. 2011 , 32 , 3183 – 3186 .
  • Karami , B. ; Eskandari , K. ; Ghasemi , A. Facile and rapid synthesis of some novel polysubstituted imidazoles by employing magnetic Fe3O4 nanoparticles as a high efficient catalyst . Turk. J Chem , 2012 , 36 , 601 – 614 .
  • Mojtahedi , M. M. ; Abaee , M. S. ; Khakbaz , M. ; Alishiri , T. ; Samianifard , M. ; Mesbah , A. W. An efficient procedure for the synthesis of α-β-unsaturated ketones: A novel application in heterocyclic systems . Synthesis 2011 , 23 , 3821 – 3826 .
  • Yang , S.-D. ; Wu , L.-Y. ; Yan , Z.-Y. ; Pan , Z.-L. ; Liang , Y.-M. A novel ionic liquid supported organocatalyst of pyrrolidine amide: Synthesis and catalyzed Claisen–Schmidt reaction . J. Mol. Cat. A 2007 , 268 , 107 – 111
  • Falck , J. R. ; He , A. ; Reddy , L. M. ; Kundu , A. ; Barma , D. K. ; Bandyopadhyay , A. ; Kamila , S. ; Akella , R. ; Bejot , R. ; Mioskowski , C. Ring expansion/homologation–aldehyde condensation cascade using tert-trihalomethylcarbinols . Org. Lett. 2006 , 8 , 4645 – 4647 .
  • Raju , S. V. N. ; Rajan , C. R. ; Srinivasan , K. V. Mukaiyama aldol reaction of silyl enol ether with aldehydes over solid sulphated zirconia with preferential syn selectivity . Synlett 1996 , 239 – 240 .
  • Hallgas , B. ; Dobos , Z. ; Agocs , A. ; Idei , M. ; Keri , G. ; Lorand , T. ; Meszaros , G. Lipophilicity and antiproliferative activity profiling of 2-benzylidencycloalkanones . J. Chromatogr. B. 2007 , 856 , 148 – 155 .
  • Kang , Y. S. ; Risbud , S. ; Rabolt , J. F. ; Stroeve , P. Synthesis and characterization of nanometer-size Fe3O4 and γ-Fe2O3 particles . Chem. Mater. 1996 , 8 , 2209 – 2211 .

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