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Volumn 35, Issue 14, 2005, Pages 1929-1937

Friedel-Crafts acylation of ferrocene catalyzed by immobilized ytterbium(III) triflate in ionic liquid

Author keywords

Acylation; Catalyst; Ferrocene; Friedel Crafts; Ionic liquid; Ytterbium triflate

Indexed keywords

FERROCENE DERIVATIVE; N BUTYLPYRIDINIUM TETRAFLUOROBORATE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG; YTTERBIUM; YTTERBIUM TRIFLATE;

EID: 22144471915     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200064991     Document Type: Article
Times cited : (23)

References (40)
  • 2
    • 17144431969 scopus 로고    scopus 로고
    • Synthesis, crystal structures, and second-order nonlinear optical properties of new chair ferrocenyl materials
    • (a) Balavioine, G. G. A.; Delaire, J.-C.; Maltery-Fanton, I.; Nakatani, K.; Bella, S. D. Synthesis, crystal structures, and second-order nonlinear optical properties of new chair ferrocenyl materials. Organometallics 1999, 18, 21-29;
    • (1999) Organometallics , vol.18 , pp. 21-29
    • Balavioine, G.G.A.1    Delaire, J.-C.2    Maltery-Fanton, I.3    Nakatani, K.4    Bella, S.D.5
  • 3
    • 0008789382 scopus 로고    scopus 로고
    • Keto-acid chloride and diketone intermediates in the acylation of ferrocene by acylene bis-acid chlorides. Crystal and molecular structure of 4-ferrocenylcarbony-4′-chlorocarbonylbiphenyl: Intermolecular association by means of strong C-H⋯O hydrogen bonds and π⋯π stacking ineractions
    • (b) Ahmed, S. Z.; Ferguson, G.; Glidewell, C. Keto-acid chloride and diketone intermediates in the acylation of ferrocene by acylene bis-acid chlorides. Crystal and molecular structure of 4-ferrocenylcarbony-4′- chlorocarbonylbiphenyl: Intermolecular association by means of strong C-H⋯O hydrogen bonds and π⋯π stacking ineractions. J. Organomet. Chem. 1999, 585, 331-334.
    • (1999) J. Organomet. Chem. , vol.585 , pp. 331-334
    • Ahmed, S.Z.1    Ferguson, G.2    Glidewell, C.3
  • 4
    • 0032546886 scopus 로고    scopus 로고
    • Asymmetric dihydroxylation reactions leading to chiral ferrocene derivatives
    • (a) Jary, W. G.; Baumgartner, J. Asymmetric dihydroxylation reactions leading to chiral ferrocene derivatives. Tetrahedron: Asymmetry 1998, 9, 2081-2085;
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 2081-2085
    • Jary, W.G.1    Baumgartner, J.2
  • 5
    • 33748906263 scopus 로고    scopus 로고
    • Simple reaction of ferrocenyl aldehydes and ketones by sodium boranuide in trifluoacetic acid: New, efficient, general preparation of alkylferrocenes
    • (b) Batthacharyya, S. Simple reaction of ferrocenyl aldehydes and ketones by sodium boranuide in trifluoacetic acid: New, efficient, general preparation of alkylferrocenes. J. Chem. Soc., Perkin Trans. 1 1996, 1381-1383.
    • (1996) J. Chem. Soc., Perkin Trans. 1 , pp. 1381-1383
    • Batthacharyya, S.1
  • 6
    • 0031571441 scopus 로고    scopus 로고
    • Facile route to ferrocifen, 1-[4-(2-dimethylaminoethoxyl)]-1-(phenyl-2- ferroceneyl-but-1-ene), first organometallic analogue of tamoxifen, by the McMurry reaction
    • Dauer, S.; Top, B.; Vaissermann, J.; Jaouen, G. Facile route to ferrocifen, 1-[4-(2-dimethylaminoethoxyl)]-1-(phenyl-2-ferroceneyl-but-1-ene), first organometallic analogue of tamoxifen, by the McMurry reaction. J. Organomet Chem. 1997, 541, 355-361.
    • (1997) J. Organomet Chem. , vol.541 , pp. 355-361
    • Dauer, S.1    Top, B.2    Vaissermann, J.3    Jaouen, G.4
  • 7
    • 0030525093 scopus 로고    scopus 로고
    • Synthesis and characterization of new perfluoroalkylated side-chain ferrocenes and ferricinium salts
    • (a) Guillon, C.; Vierling, P. Synthesis and characterization of new perfluoroalkylated side-chain ferrocenes and ferricinium salts. J. Organomet. Chem. 1996, 506, 211-220;
    • (1996) J. Organomet. Chem. , vol.506 , pp. 211-220
    • Guillon, C.1    Vierling, P.2
  • 8
    • 0034697428 scopus 로고    scopus 로고
    • Efficient region-and diastereo-controlled synthesis of 1,1′-and 1,1′,2,2′-functionalised ferrocenes and the formation of 2-oxa[3] ferrocenophanes
    • (b) Carroll, M. A.; White, A. J. P.; Widdowson, D. A.; Williams, D. J. Efficient region-and diastereo-controlled synthesis of 1,1′-and 1,1′,2,2′-functionalised ferrocenes and the formation of 2-oxa[3] ferrocenophanes. J. Chem. Soc., Perkin Trans. 1 2000, 1551-1557.
    • (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 1551-1557
    • Carroll, M.A.1    White, A.J.P.2    Widdowson, D.A.3    Williams, D.J.4
  • 10
    • 0141770598 scopus 로고
    • Certain acylation of ferrocene and some condensations involving the α-hydrogen acetylferrocene
    • (a) Hauser, C. R.; Lindsay, J. K. Certain acylation of ferrocene and some condensations involving the α-hydrogen acetylferrocene. J. Org. Chem. 1957, 22, 482-485;
    • (1957) J. Org. Chem. , vol.22 , pp. 482-485
    • Hauser, C.R.1    Lindsay, J.K.2
  • 14
    • 1342344774 scopus 로고    scopus 로고
    • Acylation of ferrocene and a 1,1′-diphosphaferrocene with acyl trifluoroacetates in the presence of trifluoromethanesulfonic (triflic) acid or some metal inflates
    • Plazuk, D.; Zakrzewski, J. Acylation of ferrocene and a 1,1′-diphosphaferrocene with acyl trifluoroacetates in the presence of trifluoromethanesulfonic (triflic) acid or some metal inflates. Synth. Commun. 2004, 34, 99-107.
    • (2004) Synth. Commun. , vol.34 , pp. 99-107
    • Plazuk, D.1    Zakrzewski, J.2
  • 15
    • 0033444259 scopus 로고    scopus 로고
    • Selective monoacylation of ferrocene: An ecofriendly procedure on the solid phase of alumina
    • Ranu, B. C.; Jana, U.; Majee, A. Selective monoacylation of ferrocene: An ecofriendly procedure on the solid phase of alumina. Green Chem. 1999, 1 (4), 33-34.
    • (1999) Green Chem. , vol.1 , Issue.4 , pp. 33-34
    • Ranu, B.C.1    Jana, U.2    Majee, A.3
  • 16
    • 0347417134 scopus 로고    scopus 로고
    • Room-temperature ionic liquids, solvents for synthesis and catalysis
    • (a) Welton, T. Room-temperature ionic liquids, solvents for synthesis and catalysis. Chem. Rev. 1999, 99, 2071-2083;
    • (1999) Chem. Rev. , vol.99 , pp. 2071-2083
    • Welton, T.1
  • 17
    • 0036809725 scopus 로고    scopus 로고
    • Ionic liquid (molten salt) phase organometallis catalysis
    • (b) Dupont, J.; Desouza, R. F.; Suarez, P. A. Z. Ionic liquid (molten salt) phase organometallis catalysis. Chem. Rev. 2002, 102, 3667-3691;
    • (2002) Chem. Rev. , vol.102 , pp. 3667-3691
    • Dupont, J.1    Desouza, R.F.2    Suarez, P.A.Z.3
  • 18
    • 0037092828 scopus 로고    scopus 로고
    • Ionic liquids: Application in catalysis
    • Zhao, D.; Wu, M.; Kou, Y.; Min, E. Ionic liquids: Application in catalysis. Catal. Today 2002, 74, 157-189.
    • (2002) Catal. Today , vol.74 , pp. 157-189
    • Zhao, D.1    Wu, M.2    Kou, Y.3    Min, E.4
  • 19
    • 0346469230 scopus 로고
    • Friedel-Crafts reaction in ambient-temperature molten salts
    • Boon, J. A.; Levisky, J. A.; Pflug, L.; Wilkes, J. S. Friedel-Crafts reaction in ambient-temperature molten salts. J. Org. Chem. 1986, 51, 480-483.
    • (1986) J. Org. Chem. , vol.51 , pp. 480-483
    • Boon, J.A.1    Levisky, J.A.2    Pflug, L.3    Wilkes, J.S.4
  • 20
    • 0038062102 scopus 로고    scopus 로고
    • 1-Ethyl-3-methylimidazoliun haloenoaluminate ionic liquids as solvents for Friedel-Crafts acylation reaction of ferrocene
    • (a) Stark, A.; MacLean, B. L.; Singer, R. D. 1-Ethyl-3-methylimidazoliun haloenoaluminate ionic liquids as solvents for Friedel-Crafts acylation reaction of ferrocene. J. Chem. Soc., Dalton Trans. 1999, 63-66;
    • (1999) J. Chem. Soc., Dalton Trans. , pp. 63-66
    • Stark, A.1    MacLean, B.L.2    Singer, R.D.3
  • 21
    • 0002741151 scopus 로고    scopus 로고
    • 1-Ethyl-3-methylimidazolium halogenoaluminate melts as reaction media for the Friedel-Crafts acylation of ferrocene
    • (b) Surette, J. K. D.; Green, L.; Singer, R. D. 1-Ethyl-3- methylimidazolium halogenoaluminate melts as reaction media for the Friedel-Crafts acylation of ferrocene. Chem. Commun. 1996, 24, 2753-2754.
    • (1996) Chem. Commun. , vol.24 , pp. 2753-2754
    • Surette, J.K.D.1    Green, L.2    Singer, R.D.3
  • 22
    • 57249089579 scopus 로고    scopus 로고
    • Friedel-Crafts acylation reaction using metal inflates in ionic liquids
    • Ross, J.; Xiao, J. Friedel-Crafts acylation reaction using metal inflates in ionic liquids. Green Chem. 2002, 4, 129-133.
    • (2002) Green Chem. , vol.4 , pp. 129-133
    • Ross, J.1    Xiao, J.2
  • 23
    • 0036625262 scopus 로고    scopus 로고
    • Rare-earth metal triflates in organic synthesis
    • Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W.-L. Rare-earth metal triflates in organic synthesis. Chem. Rev. 2002, 102, 2227-2302.
    • (2002) Chem. Rev. , vol.102 , pp. 2227-2302
    • Kobayashi, S.1    Sugiura, M.2    Kitagawa, H.3    Lam, W.-L.4
  • 24
    • 0002615814 scopus 로고
    • 3-catalyzed hydroxymethaylation reaction of silyl enol ethers with commercial formaldehyde solution
    • 3-catalyzed hydroxymethaylation reaction of silyl enol ethers with commercial formaldehyde solution. Chem. Lett. 1991, 2187-2090.
    • (1991) Chem. Lett. , pp. 2187-12090
    • Kobayashi, S.1
  • 25
    • 0030038998 scopus 로고    scopus 로고
    • Stereoselective one-pot synthesis β-lactams by Lewis acid-promoted condensation of silyketene thioacetals with imines
    • Annunziata, R.; Cinquini, M.; Cozzi, F.; Molteni, V.; Schupp, O. Stereoselective one-pot synthesis β-lactams by Lewis acid-promoted condensation of silyketene thioacetals with imines. Tetrahedron 1996, 52, 2573-2582.
    • (1996) Tetrahedron , vol.52 , pp. 2573-2582
    • Annunziata, R.1    Cinquini, M.2    Cozzi, F.3    Molteni, V.4    Schupp, O.5
  • 26
    • 0033582688 scopus 로고    scopus 로고
    • Enantioselective Diels-Alder reactions catalyzed by chiral 1,1′-(2,2′-bisacylamino)binaphalene-ytterbium complex
    • Nishida, A.; Yamanaka, M.; Nakagawa, M. Enantioselective Diels-Alder reactions catalyzed by chiral 1,1′-(2,2′-bisacylamino)binaphalene- ytterbium complex. Tetrahedron Lett. 1999, 40, 1555-1558.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 1555-1558
    • Nishida, A.1    Yamanaka, M.2    Nakagawa, M.3
  • 27
    • 0034618453 scopus 로고    scopus 로고
    • Scandium(III) triflate immoblised in ionic liquids: A novel and recycle system for Friedel-Crafts alkylation of aromatic compounds with alkenes
    • (a) Song, C. E.; Shim, W. H.; Roh, E. J.; Choi, J. H. Scandium(III) triflate immoblised in ionic liquids: A novel and recycle system for Friedel-Crafts alkylation of aromatic compounds with alkenes. Chem. Commun. 2000, 1695-1696;
    • (2000) Chem. Commun. , pp. 1695-1696
    • Song, C.E.1    Shim, W.H.2    Roh, E.J.3    Choi, J.H.4
  • 28
    • 33746606076 scopus 로고    scopus 로고
    • Ytterbium(III) triflate-catalysed preparation of calix[4] resorcinarens: Lewis assisted Brønsted acidity
    • (b) Barrett, A. G. M.; Braddock, D. C.; Henschke, J. P.; Walker, E. R. Ytterbium(III) triflate-catalysed preparation of calix[4] resorcinarens: Lewis assisted Brønsted acidity. J. Chem. Soc., Perkin Trans 1 1999, 873-878;
    • (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 873-878
    • Barrett, A.G.M.1    Braddock, D.C.2    Henschke, J.P.3    Walker, E.R.4
  • 29
    • 0030788247 scopus 로고    scopus 로고
    • The high pressure reaction of cyclopropanes with indoles catalyzed by ytterbium triflate
    • Harrington, P.; Kerr, M. A. The high pressure reaction of cyclopropanes with indoles catalyzed by ytterbium triflate. Tetrahedron Lett. 1997, 38, 5949-5952;
    • (1997) Tetrahedron Lett. , vol.38 , pp. 5949-5952
    • Harrington, P.1    Kerr, M.A.2
  • 30
    • 0034714253 scopus 로고    scopus 로고
    • Remarkable effect of lithium salts in Friedel-Crafts acylation of 2-methoxynaphthalene catalyzed by metal triflates
    • Kobayashi, S.; Komoto, I. Remarkable effect of lithium salts in Friedel-Crafts acylation of 2-methoxynaphthalene catalyzed by metal triflates. Tetrahedron 2000, 56, 6463-6465.
    • (2000) Tetrahedron , vol.56 , pp. 6463-6465
    • Kobayashi, S.1    Komoto, I.2
  • 31
    • 10644237031 scopus 로고    scopus 로고
    • Ytterbium triflate catalyzed Friedel-Crafts reaction: Facile synthesis of diaryl ketones
    • Su, W.; Jin, C. Ytterbium triflate catalyzed Friedel-Crafts reaction: Facile synthesis of diaryl ketones. Synth. Commun. 2004, 34, 4249-4256.
    • (2004) Synth. Commun. , vol.34 , pp. 4249-4256
    • Su, W.1    Jin, C.2
  • 33
    • 0034093339 scopus 로고    scopus 로고
    • Gallium nonafluorobutanesulfonates as an efficient catalyzed in Friedel-Crafts acylation
    • Matsuo, J.; Odashima, K.; Kobayashi, S. Gallium nonafluorobutanesulfonates as an efficient catalyzed in Friedel-Crafts acylation. Synlett 2000, 403-405.
    • (2000) Synlett , pp. 403-405
    • Matsuo, J.1    Odashima, K.2    Kobayashi, S.3
  • 34
    • 0000805078 scopus 로고
    • The use of oxalyl chloride and bromide for producing acid chlorides acid bromides or acid anhydrides. III
    • Adams, R.; Ulich, L. H. The use of oxalyl chloride and bromide for producing acid chlorides acid bromides or acid anhydrides. III. J. Am. Chem. Soc. 1920, 42, 599-611.
    • (1920) J. Am. Chem. Soc. , vol.42 , pp. 599-611
    • Adams, R.1    Ulich, L.H.2
  • 35
    • 0011236024 scopus 로고
    • Paranagbetuc metallocenes. Oxidation of ferrocenyl ketones
    • McDonnell, J. J.; Pochopien, D. J. Paranagbetuc metallocenes. Oxidation of ferrocenyl ketones. J. Org. Chem. 1971, 36, 2092-2098.
    • (1971) J. Org. Chem. , vol.36 , pp. 2092-2098
    • McDonnell, J.J.1    Pochopien, D.J.2
  • 36
    • 3142533338 scopus 로고    scopus 로고
    • Property of electron transfer of acylferrocenes in liquid membrane
    • Chaoyang, J.; Zihou, T.; Bin, J. Property of electron transfer of acylferrocenes in liquid membrane. J. Inorg. Chem. 1996, 12, 337-340.
    • (1996) J. Inorg. Chem. , vol.12 , pp. 337-340
    • Chaoyang, J.1    Zihou, T.2    Bin, J.3
  • 37
    • 0001582983 scopus 로고
    • Derivatives of ferrocene.II. Some reduction products of benzoylferrocene and 1,1′-dibenzoylferrocene
    • Rausch, M.; Vogel, M.; Rosenberg, H. Derivatives of ferrocene.II. Some reduction products of benzoylferrocene and 1,1′-dibenzoylferrocene. J. Org. Chem. 1957, 22, 903-906.
    • (1957) J. Org. Chem. , vol.22 , pp. 903-906
    • Rausch, M.1    Vogel, M.2    Rosenberg, H.3
  • 39
    • 0010954809 scopus 로고
    • Chem. Abstr., 70, 1969, 20203s.
    • (1969) Chem. Abstr. , vol.70
  • 40
    • 0035803658 scopus 로고    scopus 로고
    • Bis(ferrocenyl) mercury as a source of ferrocenyl molity in Pd-catalyzed reaction of carbon-carbon bond formation
    • Beletskaya, P.; Tsvetkov, A. V.; Latyshev, G. V.; Tafeenko, V. A.; Lukashev, N. V. Bis(ferrocenyl) mercury as a source of ferrocenyl molity in Pd-catalyzed reaction of carbon-carbon bond formation. J. Organomet. Chem. 2001, 637-639, 653-663.
    • (2001) J. Organomet. Chem. , vol.637-639 , pp. 653-663
    • Beletskaya, P.1    Tsvetkov, A.V.2    Latyshev, G.V.3    Tafeenko, V.A.4    Lukashev, N.V.5


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