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Volumn 36, Issue 21, 2006, Pages 3141-3148

Efficient DMF-catalyzed coupling of epoxides with CO2 under solvent-free conditions to afford cyclic carbonates

Author keywords

Carbon dioxide; Catalysis; Cyclic carbonate; DMF; Epoxide

Indexed keywords

CARBON DIOXIDE; CARBONIC ACID; EPOXIDE; N,N DIMETHYLFORMAMIDE; SOLVENT; WATER;

EID: 33750215333     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910600908744     Document Type: Article
Times cited : (52)

References (44)
  • 2
    • 0030547180 scopus 로고    scopus 로고
    • Catalysis for the reactions of epoxides and carbon dioxide
    • (b) Darensbourg, D. J.; Holtcamp, M. W. Catalysis for the reactions of epoxides and carbon dioxide. Coord. Chem. Rev. 1996, 153, 155;
    • (1996) Coord. Chem. Rev. , vol.153 , pp. 155
    • Darensbourg, D.J.1    Holtcamp, M.W.2
  • 3
    • 0030554252 scopus 로고    scopus 로고
    • The coordination chemistry of carbon dioxide and its relevance for catalysis: A critical survey
    • (c) Leitner, W. The coordination chemistry of carbon dioxide and its relevance for catalysis: A critical survey. Coord. Chem. Rev. 1996, 153, 257;
    • (1996) Coord. Chem. Rev. , vol.153 , pp. 257
    • Leitner, W.1
  • 4
    • 0001409011 scopus 로고    scopus 로고
    • The organometallic chemistry of carbon dioxide
    • (d) Gibson, D. H. The organometallic chemistry of carbon dioxide. Chem. Rev. 1996, 96, 2063.
    • (1996) Chem. Rev. , vol.96 , pp. 2063
    • Gibson, D.H.1
  • 5
    • 0000135910 scopus 로고
    • Palladium-mediated vicinal cleavage of allyl epoxides with retention of stereochemistry: A cis hydroxylation equivalent
    • (a) Trost, B. M.; Angle, S. F. Palladium-mediated vicinal cleavage of allyl epoxides with retention of stereochemistry: A cis hydroxylation equivalent. J. Am. Chem. Soc. 1985, 107, 6123;
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 6123
    • Trost, B.M.1    Angle, S.F.2
  • 6
    • 0001168982 scopus 로고
    • Palladium catalyzed reaction of butadiene monoxide with carbon dioxide
    • (b) Fujinami, T.; Suzuki, T.; Kamiya, M.; Fukukawa, S.; Sakai, S. Palladium catalyzed reaction of butadiene monoxide with carbon dioxide. Chem. Lett. 1985, 199;
    • (1985) Chem. Lett. , pp. 199
    • Fujinami, T.1    Suzuki, T.2    Kamiya, M.3    Fukukawa, S.4    Sakai, S.5
  • 7
    • 0026504140 scopus 로고
    • A simple preparation of enol ether lipids
    • (c) Pfaendler, H. R.; Mueller, F. X. A simple preparation of enol ether lipids. Synthesis 1992, 350;
    • (1992) Synthesis , pp. 350
    • Pfaendler, H.R.1    Mueller, F.X.2
  • 8
    • 0028102561 scopus 로고
    • Synthesis of α,β-unsaturated aldehydes through palladium-catalyzed regioselective hydrogen migration
    • (d) Minami, T.; Hanaoka, M. Synthesis of α,β-unsaturated aldehydes through palladium-catalyzed regioselective hydrogen migration. Tetrahedron Lett. 1994, 35, 9425;
    • (1994) Tetrahedron Lett. , vol.35 , pp. 9425
    • Minami, T.1    Hanaoka, M.2
  • 9
    • 37049088050 scopus 로고
    • Regioselectivity in the nickel-catalysed coupling of cyclic carbonates of but-3-ene-1,2-diols with organoborates
    • (e) Mizojiri, R.; Kobayashi, Y. Regioselectivity in the nickel-catalysed coupling of cyclic carbonates of but-3-ene-1,2-diols with organoborates. J. Chem. Soc., Perkin Trans. 1. 1995, 2073;
    • (1995) J. Chem. Soc., Perkin Trans. 1. , pp. 2073
    • Mizojiri, R.1    Kobayashi, Y.2
  • 10
    • 0029129852 scopus 로고
    • Enzyme-mediated enantioselective hydrolysis of cyclic carbonates
    • (f) Matsumoto, K.; Fuwa, S.; Kitajima, H. Enzyme-mediated enantioselective hydrolysis of cyclic carbonates. Tetrahedron Lett. 1995, 36, 6499;
    • (1995) Tetrahedron Lett. , vol.36 , pp. 6499
    • Matsumoto, K.1    Fuwa, S.2    Kitajima, H.3
  • 12
    • 0029937757 scopus 로고    scopus 로고
    • A practical route to enantiopure 1,2-aminoalcohols
    • (h) Chang, H.-T.; Sharpless, K. B. A practical route to enantiopure 1,2-aminoalcohols. Tetrahedron Lett. 1996, 37, 3219;
    • (1996) Tetrahedron Lett. , vol.37 , pp. 3219
    • Chang, H.-T.1    Sharpless, K.B.2
  • 14
    • 0035533485 scopus 로고    scopus 로고
    • Reactions of dichlorocarbene and arenesulfenyl chlorides with 3,4-epoxy-1-butene and vinylethylene carbonate
    • (j) Mannafov, T. G.; Berdnikov, E. A.; Samuilov, Y. D. Reactions of dichlorocarbene and arenesulfenyl chlorides with 3,4-epoxy-1-butene and vinylethylene carbonate. Russ. J. Org. Chem. 2001, 37, 339;
    • (2001) Russ. J. Org. Chem. , vol.37 , pp. 339
    • Mannafov, T.G.1    Berdnikov, E.A.2    Samuilov, Y.D.3
  • 15
    • 0036827439 scopus 로고    scopus 로고
    • Concurrent synthesis of dimethyl carbonate and ethylene glycol via transesterification of ethylene carbonate and methanol using smectite catalysts containing Mg and/or Ni
    • (k) Bhanage, B. M.; Fujita, S.-I.; He, Y.; Ikushima, Y.; Shirai, M.; Torii, K.; Arai, M. Concurrent synthesis of dimethyl carbonate and ethylene glycol via transesterification of ethylene carbonate and methanol using smectite catalysts containing Mg and/or Ni. Catal. Lett. 2002, 83, 137;
    • (2002) Catal. Lett. , vol.83 , pp. 137
    • Bhanage, B.M.1    Fujita, S.-I.2    He, Y.3    Ikushima, Y.4    Shirai, M.5    Torii, K.6    Arai, M.7
  • 16
    • 0037454053 scopus 로고    scopus 로고
    • Reactive applications of cyclic alkylene carbonates
    • (l) Clements, J. H. Reactive applications of cyclic alkylene carbonates. Ind. Eng. Chem. Res. 2003, 42, 663;
    • (2003) Ind. Eng. Chem. Res. , vol.42 , pp. 663
    • Clements, J.H.1
  • 17
    • 0038719745 scopus 로고    scopus 로고
    • Cyclic carbonate functional polymers and their applications
    • (m) Webster, D. C. Cyclic carbonate functional polymers and their applications. Progr. Org. Coat. 2003, 47, 77.
    • (2003) Progr. Org. Coat. , vol.47 , pp. 77
    • Webster, D.C.1
  • 18
    • 0033549092 scopus 로고    scopus 로고
    • Mg-Al mixed oxides as highly active acid-base catalysts for cycloaddition of carbon dioxide to epoxides
    • (a) Yamaguchi, K.; Ebitani, K.; Yoshida, T.; Yoshida, H.; Kaneda, K. Mg-Al mixed oxides as highly active acid-base catalysts for cycloaddition of carbon dioxide to epoxides. J. Am. Chem. Soc. 1999, 121, 4526;
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 4526
    • Yamaguchi, K.1    Ebitani, K.2    Yoshida, T.3    Yoshida, H.4    Kaneda, K.5
  • 20
    • 0034694679 scopus 로고    scopus 로고
    • bis-2,6-difluorophenoxide dimeric complexes of zinc and cadmium and their phosphine adducts: Lessons learned relative to carbon dioxide/cyclohexene oxide alternating copolymerization processes catalyzed by zinc phenoxides
    • (c) Darensbourg, D. J.; Wildeson, J. R.; Yarbrough, J. C.; Reibenspies, J. H. bis-2,6-Difluorophenoxide dimeric complexes of zinc and cadmium and their phosphine adducts: Lessons learned relative to carbon dioxide/cyclohexene oxide alternating copolymerization processes catalyzed by zinc phenoxides. J. Am. Chem. Soc. 2000, 122, 12487;
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 12487
    • Darensbourg, D.J.1    Wildeson, J.R.2    Yarbrough, J.C.3    Reibenspies, J.H.4
  • 22
    • 0036159906 scopus 로고    scopus 로고
    • Well-defined highly active heterogeneous catalyst system for the coupling reactions of carbon dioxide and epoxides
    • (e) Kim, H. S.; Kim, J. J.; Kwon, H. N.; Chung, M. J.; Lee, B. G.; Jang, H. G. Well-defined highly active heterogeneous catalyst system for the coupling reactions of carbon dioxide and epoxides. J. Catal. 2002, 205, 226;
    • (2002) J. Catal. , vol.205 , pp. 226
    • Kim, H.S.1    Kim, J.J.2    Kwon, H.N.3    Chung, M.J.4    Lee, B.G.5    Jang, H.G.6
  • 25
    • 0012414644 scopus 로고    scopus 로고
    • Cyclic carbonate formation from carbon dioxide and oxiranes in tetrabutylammonium halides as solvents and catalysts
    • (a) Calo, V.; Nacci, A.; Monopoli, A.; Fanizzi, A. Cyclic carbonate formation from carbon dioxide and oxiranes in tetrabutylammonium halides as solvents and catalysts. Org. Lett. 2002, 4, 2561;
    • (2002) Org. Lett. , vol.4 , pp. 2561
    • Calo, V.1    Nacci, A.2    Monopoli, A.3    Fanizzi, A.4
  • 27
    • 22944443596 scopus 로고    scopus 로고
    • Development in the green synthesis of cyclic carbonate from carbon dioxide using ionic liquids
    • (c) Sun, J.; Fujita, S.; Arai, M. Development in the green synthesis of cyclic carbonate from carbon dioxide using ionic liquids. J. Organomet. Chem. 2005, 690, 3490.
    • (2005) J. Organomet. Chem. , vol.690 , pp. 3490
    • Sun, J.1    Fujita, S.2    Arai, M.3
  • 30
    • 0043068104 scopus 로고    scopus 로고
    • A novel and effective Ni complex catalyst system for the coupling reactions of carbon dioxide and epoxides
    • (c) Li, F.; Xia, C.; Xu, L.; Sun, W.; Chen, G. A novel and effective Ni complex catalyst system for the coupling reactions of carbon dioxide and epoxides. Chem. Commun. 2003, 2042;
    • (2003) Chem. Commun. , pp. 2042
    • Li, F.1    Xia, C.2    Xu, L.3    Sun, W.4    Chen, G.5
  • 31
    • 0242432419 scopus 로고    scopus 로고
    • Chemical fixation of carbon dioxide catalyzed by binaphthyldiamino Zn, Cu, and Co Salen-type complexes
    • (d) Shen, Y.-M.; Duan, W.-L.; Shi, M. Chemical fixation of carbon dioxide catalyzed by binaphthyldiamino Zn, Cu, and Co Salen-type complexes. J. Org. Chem. 2003, 68, 1559;
    • (2003) J. Org. Chem. , vol.68 , pp. 1559
    • Shen, Y.-M.1    Duan, W.-L.2    Shi, M.3
  • 32
    • 0041564369 scopus 로고    scopus 로고
    • Phenol and organic bases co-catalyzed chemical fixation of carbon dioxide with terminal epoxides to form cyclic carbonates
    • (e) Shen, Y.-M.; Duan, W.-L.; Shi, M. Phenol and organic bases co-catalyzed chemical fixation of carbon dioxide with terminal epoxides to form cyclic carbonates. Adv. Synth. Catal. 2003, 345, 337;
    • (2003) Adv. Synth. Catal. , vol.345 , pp. 337
    • Shen, Y.-M.1    Duan, W.-L.2    Shi, M.3
  • 33
    • 3042698413 scopus 로고    scopus 로고
    • Novel methodologies for the synthesis of cyclic carbonates
    • (f) Yoshida, M.; Ihara, M. Novel methodologies for the synthesis of cyclic carbonates. Chem. Eur. J. 2004, 10, 2886;
    • (2004) Chem. Eur. J. , vol.10 , pp. 2886
    • Yoshida, M.1    Ihara, M.2
  • 34
    • 11844277005 scopus 로고    scopus 로고
    • 2 affording cyclic carbonates under solvent-free conditions
    • 2 affording cyclic carbonates under solvent-free conditions. J. Org. Chem. 2005, 70, 381;
    • (2005) J. Org. Chem. , vol.70 , pp. 381
    • Jiang, J.-L.1    Gao, F.2    Hua, R.3    Qiu, X.4
  • 35
    • 31444454154 scopus 로고    scopus 로고
    • Synthesis of heterobimetallic Ru-Mn complexes and the coupling reactions of epoxides with carbon dioxide catalyzed by these complexes
    • (h) Man, M. L.; Lam, K. C.; Sit, W. N.; Ng, S. M.; Zhou, Z.; Lin, Z.; Lau, C. P. Synthesis of heterobimetallic Ru-Mn complexes and the coupling reactions of epoxides with carbon dioxide catalyzed by these complexes. Chem. Eur. J. 2006, 12, 1004.
    • (2006) Chem. Eur. J. , vol.12 , pp. 1004
    • Man, M.L.1    Lam, K.C.2    Sit, W.N.3    Ng, S.M.4    Zhou, Z.5    Lin, Z.6    Lau, C.P.7
  • 36
    • 0035886887 scopus 로고    scopus 로고
    • Enantioselective organocatalysis
    • (a) Dalko, P. I.; Moisan, L. Enantioselective organocatalysis. Angew. Chem. Int. Ed. 2001, 40, 3726;
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 3726
    • Dalko, P.I.1    Moisan, L.2
  • 37
    • 0034807741 scopus 로고    scopus 로고
    • New strategies in organic catalysis: The first enantioselective organocatalytic Friedel-Crafts alkylation
    • and references therein
    • (b) Paras, N. A.; MacMillian, D. W. C. New strategies in organic catalysis: The first enantioselective organocatalytic Friedel-Crafts alkylation. J. Am. Chem. Soc. 2001, 123, 4370, and references therein;
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 4370
    • Paras, N.A.1    MacMillian, D.W.C.2
  • 38
    • 0037126839 scopus 로고    scopus 로고
    • A highly enantioselective and general conjugate addition of thiols to cyclic enones with an organic catalyst
    • (c) McDaid, P.; Chen, Y.; Deng, L. A highly enantioselective and general conjugate addition of thiols to cyclic enones with an organic catalyst. Angew. Chem. Int. Ed. 2002, 41, 338;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 338
    • McDaid, P.1    Chen, Y.2    Deng, L.3
  • 40
    • 0141619399 scopus 로고    scopus 로고
    • Polymer-supported organic catalysts
    • (e) Benaglia, M.; Puglisi, A.; Cozzi, F. Polymer-supported organic catalysts. Chem. Rev. 2003, 103, 3401;
    • (2003) Chem. Rev. , vol.103 , pp. 3401
    • Benaglia, M.1    Puglisi, A.2    Cozzi, F.3
  • 41
    • 6044269452 scopus 로고    scopus 로고
    • In the golden age of organocatalysis
    • (f) Dalko, P. I.; Moisan, L. In the golden age of organocatalysis. Angew. Chem. Int. Ed. 2004, 43, 5138;
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 5138
    • Dalko, P.I.1    Moisan, L.2
  • 42
    • 21244473265 scopus 로고    scopus 로고
    • Dihydroxyacetone in amino acid catalyzed Mannich-type reactions
    • (g) Westermann, B.; Neuhaus, C. Dihydroxyacetone in amino acid catalyzed Mannich-type reactions. Angew. Chem. Int. Ed. 2005, L44, 4077;
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 4077
    • Westermann, B.1    Neuhaus, C.2
  • 44
    • 0034619630 scopus 로고    scopus 로고
    • Chemical fixation of carbon dioxide to styrene carbonate under supercritical conditions with DMF in the absence of any additional catalysts
    • Kawanami, H.; Ikushima, Y. Chemical fixation of carbon dioxide to styrene carbonate under supercritical conditions with DMF in the absence of any additional catalysts. Chem. Commun. 2000, 2089.
    • (2000) Chem. Commun. , pp. 2089
    • Kawanami, H.1    Ikushima, Y.2


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