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Volumn 55, Issue 8, 2012, Pages 1614-1619

Iron catalyzed Michael addition: Chloroferrate ionic liquids as efficient catalysts under microwave conditions

Author keywords

Catalysis; Ionic liquids; Iron; Lewis acid; Michael addition; Microwave chemistry

Indexed keywords

EFFICIENT CATALYSTS; IONIC STRUCTURE; KETO ESTER; LEWIS ACID; LIQUID CATALYST; MICHAEL ADDITIONS; MICROWAVE CHEMISTRY; MICROWAVE CONDITIONS; SOLVENT FREE; TETRACHLOROFERRATE;

EID: 84866173165     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-012-4657-z     Document Type: Article
Times cited : (15)

References (26)
  • 1
    • 0347417134 scopus 로고    scopus 로고
    • Room-temperature ionic liquids. Solvents for synthesis and catalysis
    • (a) (b) Wasserscheid P, Keim W. Ionic liquids-new "solutions" for transition metal catalysis. Angew Chem Int Ed, 2000, 39: 3772-3789
    • (a) Welton T. Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev, 1999, 99: 2071-2084; (b) Wasserscheid P, Keim W. Ionic liquids-new "solutions" for transition metal catalysis. Angew Chem Int Ed, 2000, 39: 3772-3789
    • (1999) Chem Rev , vol.99 , pp. 2071-2084
    • Welton, T.1
  • 2
    • 0242363674 scopus 로고    scopus 로고
    • Ionic liquids-solvents of the futuré
    • Rodgers RD, Seddon KR. Ionic liquids-solvents of the futuré Science, 2003, 302: 792-793
    • (2003) Science , vol.302 , pp. 792-793
    • Rodgers, R.D.1    Seddon, K.R.2
  • 3
    • 0004145285 scopus 로고    scopus 로고
    • (a) Weihnheim: Wiley-VCH, Germany (b) Olivier-Bourbigou H, Magna L, Ionic liquids: Perspectives for organic and catalytic reactions. J Mol Catal A, 2002, 182-183: 419-437
    • (a) Wasserscheid P, Welton T. Ionic Liquids in Synthesis. Weihnheim: Wiley-VCH, Germany, 2003; (b) Olivier-Bourbigou H, Magna L, Ionic liquids: Perspectives for organic and catalytic reactions. J Mol Catal A, 2002, 182-183: 419-437
    • (2003) Ionic Liquids in Synthesis
    • Wasserscheid, P.1    Welton, T.2
  • 4
    • 0036809725 scopus 로고    scopus 로고
    • Ionic liquid (molten salt) phase organometallic catalysis
    • DOI 10.1021/cr010338r
    • Dupont J, deSouza RF, Suarez PAZ. Ionic liquid (molten salt) phase organometallic catalysis. Chem Rev, 2002, 102: 3667-3692 (Pubitemid 35353956)
    • (2002) Chemical Reviews , vol.102 , Issue.10 , pp. 3667-3692
    • Dupont, J.1    De Souza, R.F.2    Suarez, P.A.Z.3
  • 5
    • 11144323895 scopus 로고    scopus 로고
    • Iron-catalyzed reactions in organic synthesis
    • DOI 10.1021/cr040664h
    • Bolm C, Legros J, Le Paih J, Zani L. Iron-catalyzed reactions in organic synthesis. Chem Rev, 2004, 104: 6217-6254 (Pubitemid 40034050)
    • (2004) Chemical Reviews , vol.104 , Issue.12 , pp. 6217-6254
    • Bolm, C.1    Legros, J.2    Le Paih, J.3    Zani, L.4
  • 7
    • 81155123963 scopus 로고    scopus 로고
    • From solvent to sustainable catalysis. Chloroferrate ionic liquids in synthesis
    • Bica K, Leder S, Gaertner P. From solvent to sustainable catalysis. Chloroferrate ionic liquids in synthesis. Curr Org Synth, 2011, 8: 824-839
    • (2011) Curr Org Synth , vol.8 , pp. 824-839
    • Bica, K.1    Leder, S.2    Gaertner, P.3
  • 8
    • 0035854627 scopus 로고    scopus 로고
    • Friedel-Crafts acylation of aromatics catalysed by supported ionic liquids
    • DOI 10.1016/S0926-860X(01)00531-2, PII S0926860X01005312
    • Valkenberg MH, deCastro C, Holderich WF, Friedel-Crafts acylation of aromatics catalysed by supported ionic liquids. Appl Catal A, 2001, 215: 185-190 (Pubitemid 32573606)
    • (2001) Applied Catalysis A: General , vol.215 , Issue.1-2 , pp. 185-190
    • Valkenberg, M.H.1    DeCastro, C.2    Holderich, W.F.3
  • 9
    • 53849091676 scopus 로고    scopus 로고
    • Metal-containing ionic liquids as efficient catalysts for hydroxymethylation in water
    • Bica K, Gaertner P. Metal-containing ionic liquids as efficient catalysts for hydroxymethylation in water. Eur J Org Chem, 2008, 20: 3453-3456
    • (2008) Eur J Org Chem , vol.20 , pp. 3453-3456
    • Bica, K.1    Gaertner, P.2
  • 10
    • 33644770072 scopus 로고    scopus 로고
    • An iron-containing ionic liquid as recyclable catalyst for aryl Grignard cross-coupling of alkyl halides
    • DOI 10.1021/ol052965z
    • Bica K, Gaertner P. An iron-containing ionic liquid as recyclable catalyst for aryl grignard cross-coupling of alkyl halides. Org Lett, 2006, 8: 733-735 (Pubitemid 43342002)
    • (2006) Organic Letters , vol.8 , Issue.4 , pp. 733-735
    • Bica, K.1    Gaertner, P.2
  • 11
    • 14644435161 scopus 로고    scopus 로고
    • Microwave-assisted Michael addition of some pyrimidine and purine nucleobases with α,β-unsaturated esters: A rapid entry into carboacyclic nucleoside synthesis
    • DOI 10.1055/s-2004-834950, Z17004SS
    • (a) Khalafi-Nezhad A, Zarea A, Soltani Rad MN, Mokhtari B, Parhami A. Microwave-assisted michael addition of some pyrimidine and purine nucleobases with a, b-unsaturated esters: A rapid entry into carboacyclic nucleoside synthesis. Synthesis, 2005, 3: 419-424; (b) Kawabata T, Mizugaki T, Ebitani K, Kaneda KJ. A novel montmorillonite-enwrapped scandium as a heterogeneous catalyst for michael reaction. J Am Chem Soc, 2003, 125: 10486-10487; (c) Guo R, Morris RH, Song DJ. Enantioselective tandem Michael addition/H2-hydrogenation catalyzed by ruthenium hydride borohydride complexes containing ruthenium hydride borohydride complexes -aminophosphine ligands. J Am Chem Soc, 2005, 127: 516-517; (d) Ishii T, Fujioka S, Sekiguchi Y, Kotsuki HJ. A new class of chiral pyrrolidine-pyridine conjugate base catalysts for use in asymmetric michael addition reactions. J Am Chem Soc, 2004, 126: 9558-9559 (Pubitemid 40321731)
    • (2005) Synthesis , Issue.3 , pp. 419-424
    • Khalafi-Nezhad, A.1    Zarea, A.2    Soltani Rad, M.N.3    Mokhtari, B.4    Parhami, A.5
  • 12
    • 33847086686 scopus 로고
    • Nickel-catalyzed Michael additions of β-dicarbonyls
    • (b) Brunner H, Kraus JJ. Asymmetric catalysis: Part 41: Enantioselective michael additions catalyzed by Co(II)/1,2-diphenylethylenediamine. Mol Catal, 1989, 49: 133-142
    • (a) Nelson JH, Howells PN, DeLullo GC, Landen GL, Henry RA. Nickel-catalyzed Michael additions of β-dicarbonyls. J Org Chem, 1980, 45: 1246-1249; (b) Brunner H, Kraus JJ. Asymmetric catalysis: Part 41: Enantioselective michael additions catalyzed by Co(II)/1,2- diphenylethylenediamine. Mol Catal, 1989, 49: 133-142
    • (1980) J Org Chem , vol.45 , pp. 1246-1249
    • Nelson, J.H.1    Howells, P.N.2    Delullo, G.C.3    Landen, G.L.4    Henry, R.A.5
  • 13
    • 2742606973 scopus 로고    scopus 로고
    • Transition-metal catalysis of the Michael reaction of 1,3-dicarbonyl compounds and acceptor-activated alkenes
    • (a) Christoffers J. Transition-metal catalysis of the Michael reaction of 1,3-dicarbonyl compounds and acceptor-activated alkenes. Eur J Org Chem, 1998, 1259-1266; (b) Christoffers J. Novel chemoselective and diastereoselective iron(III)-catalysed Michael reactions of 1,3-dicarbonyl compounds and enones. J Chem Soc, Perkin Trans, 1997, 1: 3141-3150; (c) Mekonnen A, Carlson R. Lewis acid catalyzed conjugate addition and the formation of heterocycles using Michael acceptors under solvent-free conditions. Eur J Org Chem, 2006, 2005-2013 (Pubitemid 128535890)
    • (1998) European Journal of Organic Chemistry , Issue.7 , pp. 1259-1266
    • Christoffers, J.1
  • 14
    • 0000865084 scopus 로고    scopus 로고
    • Iron(III) catalysis of the Michael reaction of 1,3-dicarbonyl compounds and enones
    • Christoffers J. Iron(III) catalysis of the Michael reaction of 1,3-dicarbonyl compounds and enones. Chem Commun, 1997, 10: 943-944 (Pubitemid 127696176)
    • (1997) Chemical Communications , Issue.10 , pp. 943-944
    • Christoffers, J.1
  • 15
    • 0042836600 scopus 로고    scopus 로고
    • 3+-exchanged fluorotetrasilicic mica as an active and reusable catalyst for Michael reaction
    • DOI 10.1016/j.tetlet.2003.08.048
    • Shimizu K, Miyagi M, Kan-no T, Kodama T, Kitayama Y. Fe3+-exchanged fluorotetrasilicic mica as an active and reusable catalyst for the Michael reaction. Tetrahedron Lett, 2003, 44: 7421-7424 (Pubitemid 37102969)
    • (2003) Tetrahedron Letters , vol.44 , Issue.40 , pp. 7421-7424
    • Shimizu, K.-I.1    Miyagi, M.2    Kan-no, T.3    Kodama, T.4    Kitayama, Y.5
  • 16
    • 33645324052 scopus 로고    scopus 로고
    • Conjugate addition of indoles with electron-deficient olefins catalyzed by Fe-exchanged montmorillonite K10
    • Singh D, Singh P, Samant S. Conjugate addition of indoles with electron-deficient olefins catalyzed by Fe-exchanged montmorillonite K10. Synth Commun, 2006, 36: 1265-1271
    • (2006) Synth Commun , vol.36 , pp. 1265-1271
    • Singh, D.1    Singh, P.2    Samant, S.3
  • 17
    • 22244482818 scopus 로고    scopus 로고
    • Investigations into the metal species of the homogeneous iron(III) catalyzed Michael addition reactions
    • DOI 10.1039/b501204j
    • (a) Bauer M, Kauf T, Christoffers J, Bertagnollia H. Investigations into the metal species of the homogeneous iron(III) catalyzed Michael addition reactions. Phys Chem Chem Phys, 2005, 7: 2664-2670; (b) Pelzer S, Kauf T, van Wüllen C, Christoffers J. Catalysis of the Michael reaction by iron(III): Calculations, mechanistic insights and experimental consequences. Organomet Chem, 2003, 684: 308-314 (Pubitemid 40991663)
    • (2005) Physical Chemistry Chemical Physics , vol.7 , Issue.13 , pp. 2664-2670
    • Bauer, M.1    Kauf, T.2    Christoffers, J.3    Bertagnolli, H.4
  • 18
    • 12444281014 scopus 로고    scopus 로고
    • Coordination of iron(III) cations to β-keto esters as studied by electrospray mass spectrometry: Implications for iron-catalyzed michael addition reactions
    • DOI 10.1002/chem.200400715
    • Trage C, Schröder D, Schwarz H. Coordination of iron(III) cations to β-keto esters as studied by electrospray mass spectrometry: Implications for iron-catalyzed Michael addition reactions. Chem Eur J, 2005, 11: 619-627 (Pubitemid 40143061)
    • (2005) Chemistry - A European Journal , vol.11 , Issue.2 , pp. 619-627
    • Trage, C.1    Schroder, D.2    Schwarz, H.3
  • 19
    • 0037034920 scopus 로고    scopus 로고
    • Metal catalysed Michael additions in ionic liquids
    • (a) Dell'Anna MM, Gallo V, Mastrorilli P, Nobile CF, Romanazzi G, Suranna GP. Metal catalysed Michael additions in ionic liquids. Chem Commun, 2002, 434-435; (b) Gallo V, Mastrorilli P, Nobile CF, Romanazzi G, Suranna GP. How does the presence of impurities change the performance of catalytic systems in ionic liquids? A case study: the Michael addition of acetylacetone to methyl vinyl ketone. J Chem Soc, Dalton Trans, 2002, 4339-4342 (Pubitemid 34252460)
    • (2002) Chemical Communications , Issue.5 , pp. 434-435
    • Dell'Anna, M.M.1    Gallo, V.2    Mastrorilli, P.3    Nobile, C.F.4    Romanazzi, G.5    Suranna, G.P.6
  • 20
    • 22244486653 scopus 로고    scopus 로고
    • Ionic liquid as catalyst and reaction medium. The dramatic influence of a task-specific ionic liquid, [bmIm]OH, in Michael addition of active methylene compounds to conjugated ketones, carboxylic esters, and nitriles
    • DOI 10.1021/ol051004h
    • (a) Ranu BC, Banerjee S. Ionic liquid as catalyst and reaction medium. the dramatic influence of a task-specific ionic liquid, [bmIm]OH, in michael addition of active methylene compounds to conjugated ketones, carboxylic esters, and nitriles. Org Lett, 2005, 7: 3049-3052; (b) Xu J, Qian C, Wu Q, Lin X. A fast and highly efficient protocol for Michael addition of N-heterocycles to α,β-unsaturated compound using basic ionic liquid [bmIm]OH as catalyst and green solvent. Tetrahedron, 2006, 63: 986-990; (c) Ranu BC, Banerjee S, Jana R. Ionic liquid as catalyst and solvent: the remarkable effect of a basic ionic liquid, [bmIm]OH on Michael addition and alkylation of active methylene compounds. Tetrahedron, 2006, 63: 776-782 (Pubitemid 40992628)
    • (2005) Organic Letters , vol.7 , Issue.14 , pp. 3049-3052
    • Ranu, B.C.1    Banerjee, S.2
  • 21
    • 0001178682 scopus 로고
    • Organic reactions at high pressure. A Robinson annulation sequence initiated by Michael addition of activated cycloalkanones with hindered enones
    • Dauben WG, Bunce RA. Organic reactions at high pressure. A Robinson annulation sequence initiated by Michael addition of activated cycloalkanones with hindered enones. J Org Chem, 1983, 48: 4642-4648
    • (1983) J Org Chem , vol.48 , pp. 4642-4648
    • Dauben, W.G.1    Bunce, R.A.2
  • 23
    • 27844501154 scopus 로고    scopus 로고
    • K10 montmorillonite catalysis. CC Bond formation by catalyzed conjugate addition and alkoxyalkylation of 1, 3-dicarbonyl compounds
    • Soriente A, Arienzo R, De Rosa M, Spinella A, Scettri A, Palombi L. K10 montmorillonite catalysis. CC Bond formation by catalyzed conjugate addition and alkoxyalkylation of 1, 3-dicarbonyl compounds. Green Chem, 1999, 1: 157-162
    • (1999) Green Chem , vol.1 , pp. 157-162
    • Soriente, A.1    Arienzo, R.2    De Rosa, M.3    Spinella, A.4    Scettri, A.5    Palombi, L.6
  • 24
    • 4243096265 scopus 로고    scopus 로고
    • Microwave-promoted organic synthesis using ionic liquids: A mini review
    • For a review: (a) Leadbeater NE, Torenius HM, Tye H. Microwave-promoted organic synthesis using ionic liquids: A mini review. Combinatorial Chemistry and High Throughput Screening, 2004, 7: 511-528; (b) Roberts BA, Straus CR. Toward rapid, "green", predictable microwave-assisted synthesis. Acc Chem Res, 2005, 38: 653-661 (Pubitemid 39108268)
    • (2004) Combinatorial Chemistry and High Throughput Screening , vol.7 , Issue.5 , pp. 511-528
    • Leadbeater, N.E.1    Torenius, H.M.2    Tye, H.3
  • 26
    • 0037012872 scopus 로고    scopus 로고
    • A study of the ionic liquid mediated microwave heating of organic solvents
    • DOI 10.1021/jo016297g
    • Leadbeater NE, Torenius HM. A study of the ionic liquid mediated microwave heating of organic solvents. J Org Chem, 2002, 67: 3145-3148 (Pubitemid 34457282)
    • (2002) Journal of Organic Chemistry , vol.67 , Issue.9 , pp. 3145-3148
    • Leadbeater, N.E.1    Torenius, H.M.2


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