메뉴 건너뛰기




Volumn 116, Issue , 2014, Pages 475-483

CO2 as a C1-organic building block: Enantioselective electrocarboxylation of aromatic ketones with CO2catalyzed by cinchona alkaloids under mild conditions

Author keywords

Alkaloid; Aromatic ketones; CO2; Electrocarboxylation; Enantioselective

Indexed keywords

AROMATIC KETONES; CATH-ODE MATERIALS; ELECTROCARBOXYLATION; ELECTROCHEMICAL BEHAVIORS; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE; OPTIMIZED CONDITIONS; REACTION CONDITIONS;

EID: 84889998970     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.electacta.2013.11.001     Document Type: Article
Times cited : (52)

References (50)
  • 1
    • 84856524789 scopus 로고    scopus 로고
    • Umwandlung von Kohlendioxid mit Übergangsmetall- Homogenkatalysatoren: Eine molekulare Lösung für ein globales Problem?
    • M. Cokoja, C. Bruckmeier, B. Rieger, W.A. Herrmann, and F.E. Kühn Umwandlung von Kohlendioxid mit Übergangsmetall-Homogenkatalysatoren: eine molekulare Lösung für ein globales Problem? Angew. Chem. 123 2011 8662
    • (2011) Angew. Chem. , vol.123 , pp. 8662
    • Cokoja, M.1    Bruckmeier, C.2    Rieger, B.3    Herrmann, W.A.4    Kühn, F.E.5
  • 6
    • 84863683008 scopus 로고    scopus 로고
    • C-C Bond Formation with Carbon Dioxide Promoted by a Silver Catalyst
    • S. Kikuchi, K. Sekine, T. Ishida, and T. Yamada C-C Bond Formation with Carbon Dioxide Promoted by a Silver Catalyst Angew. Chem. Int. Ed. 51 2012 1
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 1
    • Kikuchi, S.1    Sekine, K.2    Ishida, T.3    Yamada, T.4
  • 10
    • 61449173827 scopus 로고    scopus 로고
    • Electrochemical activation of carbon dioxide for synthesis of dimethyl carbonate in an ionic liquid
    • D.-D. Yuan, C.-H. Yan, B. Lu, H.-X. Wang, C.-M. Zhong, and Q.-H. Cai Electrochemical activation of carbon dioxide for synthesis of dimethyl carbonate in an ionic liquid Electrochim. Acta 54 2009 2912
    • (2009) Electrochim. Acta , vol.54 , pp. 2912
    • Yuan, D.-D.1    Yan, C.-H.2    Lu, B.3    Wang, H.-X.4    Zhong, C.-M.5    Cai, Q.-H.6
  • 11
    • 0034606884 scopus 로고    scopus 로고
    • The reaction of amines with an electrogenerated base. Improved synthesis of arylcarbamic esters
    • M. Feroci, A. Inesi, and L. Rossi The reaction of amines with an electrogenerated base. Improved synthesis of arylcarbamic esters Tetrahedron Lett. 41 2000 963
    • (2000) Tetrahedron Lett. , vol.41 , pp. 963
    • Feroci, M.1    Inesi, A.2    Rossi, L.3
  • 14
    • 43449120697 scopus 로고    scopus 로고
    • Efficient electrochemical dicarboxylations of arylacetylenes with carbon dioxide using nickel as the cathode
    • G.-Q. Yuan, H.-F. Jiang, and C. Lin Efficient electrochemical dicarboxylations of arylacetylenes with carbon dioxide using nickel as the cathode Tetrahedron 64 2008 5866
    • (2008) Tetrahedron , vol.64 , pp. 5866
    • Yuan, G.-Q.1    Jiang, H.-F.2    Lin, C.3
  • 16
    • 40849111144 scopus 로고    scopus 로고
    • Electrocarboxylation of 2-methylhalogen-9,10-anthraquinones
    • M.C.E. Bandeira, and G. Maia Electrocarboxylation of 2-methylhalogen-9, 10-anthraquinones Electrochim. Acta. 53 2008 4512
    • (2008) Electrochim. Acta. , vol.53 , pp. 4512
    • Bandeira, M.C.E.1    Maia, G.2
  • 17
    • 34948882355 scopus 로고    scopus 로고
    • Electrocarboxylation of aromatic ketones: Influence of operative parameters on the competition between ketyl and ring carboxylation
    • O. Scialdone, A. Galia, A.A. Isse, A. Gennaro, M.A. Sabatino, R. Leone, and G. Filardo Electrocarboxylation of aromatic ketones: Influence of operative parameters on the competition between ketyl and ring carboxylation J. Electroanal. Chem. 609 2007 8
    • (2007) J. Electroanal. Chem. , vol.609 , pp. 8
    • Scialdone, O.1    Galia, A.2    Isse, A.A.3    Gennaro, A.4    Sabatino, M.A.5    Leone, R.6    Filardo, G.7
  • 18
    • 33745371019 scopus 로고    scopus 로고
    • CO2 as a C1-organic building block: Electrocarboxylation of aromatic ketones. A quantitative study of the effect of the concentration of substrate and of carbon dioxide on the selectivity of the process
    • O. Scialdone, C. Amatore, A. Galia, and G. Filardo CO2 as a C1-organic building block: Electrocarboxylation of aromatic ketones. A quantitative study of the effect of the concentration of substrate and of carbon dioxide on the selectivity of the process J. Electroanal. Chem. 592 2006 163
    • (2006) J. Electroanal. Chem. , vol.592 , pp. 163
    • Scialdone, O.1    Amatore, C.2    Galia, A.3    Filardo, G.4
  • 19
    • 9744268958 scopus 로고    scopus 로고
    • Chiral Synthesis on Catalysts Immobilized in Microporous and Mesoporous Materials
    • C. Li Chiral Synthesis on Catalysts Immobilized in Microporous and Mesoporous Materials Catal. Rev. 46 2004 419
    • (2004) Catal. Rev. , vol.46 , pp. 419
    • Li, C.1
  • 20
    • 76449097139 scopus 로고    scopus 로고
    • Electrochemical synthesis and optical properties of helical polyaniline nanofibers
    • S.-H. Weng, Z.-H. Lin, L.-X. Chen, and J.-Z. Zhou Electrochemical synthesis and optical properties of helical polyaniline nanofibers Electrochimica Acta 55 2010 2727
    • (2010) Electrochimica Acta , vol.55 , pp. 2727
    • Weng, S.-H.1    Lin, Z.-H.2    Chen, L.-X.3    Zhou, J.-Z.4
  • 21
    • 57849153303 scopus 로고    scopus 로고
    • Electrogenerated N-heterocyclic carbene: N-acylation of chiral oxazolidin-2-ones in ionic liquids
    • I. Chiarotto, M.M.M. Feeney, M. Feroci, and A. Inesi Electrogenerated N-heterocyclic carbene: N-acylation of chiral oxazolidin-2-ones in ionic liquids Electrochimica Acta 54 2009 1638
    • (2009) Electrochimica Acta , vol.54 , pp. 1638
    • Chiarotto, I.1    Feeney, M.M.M.2    Feroci, M.3    Inesi, A.4
  • 22
    • 24344465813 scopus 로고    scopus 로고
    • Stereoselective synthesis of optically active 2-alkylpiperidines utilizing electrochemical oxidation as a key step
    • O. Onomura, Y. Kanda, M. Imai, and Y. Matsumura Stereoselective synthesis of optically active 2-alkylpiperidines utilizing electrochemical oxidation as a key step Electrochimica Acta 50 2005 4926
    • (2005) Electrochimica Acta , vol.50 , pp. 4926
    • Onomura, O.1    Kanda, Y.2    Imai, M.3    Matsumura, Y.4
  • 24
    • 34548314348 scopus 로고    scopus 로고
    • Asymmetric catalysis of metal complexes with non-planar ONNO ligands: Salen, salalen and salan
    • K. Matsumoto, B. Saito, and T. Katsuki Asymmetric catalysis of metal complexes with non-planar ONNO ligands: salen, salalen and salan Chem. Commun. 2007 3619
    • (2007) Chem. Commun. , pp. 3619
    • Matsumoto, K.1    Saito, B.2    Katsuki, T.3
  • 25
    • 0028332523 scopus 로고
    • Asymmetric Trifluoromethylation of Aldehydes and Ketones with Trifluoromethyltrimethylsilane Catalyzed by Chiral Quaternary Ammonium Fluorides
    • K. Iseki, T. Nagai, and Y. Kobayashi Asymmetric Trifluoromethylation of Aldehydes and Ketones with Trifluoromethyltrimethylsilane Catalyzed by Chiral Quaternary Ammonium Fluorides Tetrahedron Lett. 35 1994 3137
    • (1994) Tetrahedron Lett. , vol.35 , pp. 3137
    • Iseki, K.1    Nagai, T.2    Kobayashi, Y.3
  • 26
    • 83755195537 scopus 로고    scopus 로고
    • Asymmetric Synthesis of β-Adrenergic Blockers through Multistep One-Pot Transformations Involving in Situ Chiral Organocatalyst Formation
    • S.-W. Wei, R. Messerer, and S.B. Tsogoeva Asymmetric Synthesis of β-Adrenergic Blockers through Multistep One-Pot Transformations Involving In Situ Chiral Organocatalyst Formation Chem. Eur. J. 17 2011 14380
    • (2011) Chem. Eur. J. , vol.17 , pp. 14380
    • Wei, S.-W.1    Messerer, R.2    Tsogoeva, S.B.3
  • 27
    • 26844549565 scopus 로고    scopus 로고
    • Iridium-supported catalyst for enantioselective hydrogenation of 1-phenyl-1,2-propanedione: The effects of the addition of promoter and the modifier concentration
    • T. Marzialetti, J.L.G. Fierro, and P. Reyes Iridium-supported catalyst for enantioselective hydrogenation of 1-phenyl-1,2-propanedione: The effects of the addition of promoter and the modifier concentration Catal. Taday 107-108 2005 235
    • (2005) Catal. Taday , vol.107-108 , pp. 235
    • Marzialetti, T.1    Fierro, J.L.G.2    Reyes, P.3
  • 28
    • 80555149230 scopus 로고    scopus 로고
    • Ruthenium-catalysed transfer hydrogenation reactions with dimethylamine borane
    • T.D. Nixon, M.K. Whittlesey, and J.M.J. Williams Ruthenium-catalysed transfer hydrogenation reactions with dimethylamine borane Tetrahedron Lett. 52 2011 6652
    • (2011) Tetrahedron Lett. , vol.52 , pp. 6652
    • Nixon, T.D.1    Whittlesey, M.K.2    Williams, J.M.J.3
  • 29
    • 0035858737 scopus 로고    scopus 로고
    • Enantioselective hydrogenation of isophorone over Pd catalysts in the presence of(-)-dihydroapovincaminic acid ethyl ester the effect of reduction method of Pd blacks on the enantiomeric excess
    • G. Farkas, É. ŚIpos, A. Tungler, A. Sárkány, and J.L. Figueiredo Enantioselective hydrogenation of isophorone over Pd catalysts in the presence of(-)-dihydroapovincaminic acid ethyl ester The effect of reduction method of Pd blacks on the enantiomeric excess J. Mol. Catal. A: Chem. 170 2001 101
    • (2001) J. Mol. Catal. A: Chem. , vol.170 , pp. 101
    • Farkas, G.1    Śipos, E.2    Tungler, A.3    Sárkány, A.4    Figueiredo, J.L.5
  • 30
    • 80055063072 scopus 로고    scopus 로고
    • Synthesis of a new class of ligands derived from isosorbide and their application to asymmetric reduction of aromatic ketones by transfer hydrogenation
    • K.D. Huynh, H. Ibrahim, E. Kolodziej, M. Toffano, and G. Vo-Thanh Synthesis of a new class of ligands derived from isosorbide and their application to asymmetric reduction of aromatic ketones by transfer hydrogenation New J. Chem. 35 2011 2622
    • (2011) New J. Chem. , vol.35 , pp. 2622
    • Huynh, K.D.1    Ibrahim, H.2    Kolodziej, E.3    Toffano, M.4    Vo-Thanh, G.5
  • 31
    • 0346502716 scopus 로고    scopus 로고
    • Diastereoselective Electrochemical Carboxylation of Chiral α-Bromocarboxylic Acid Derivatives: An Easy Access to Unsymmetrical Alkylmalonic Ester Derivatives
    • M. Feroci, M. Orsini, L. Palombi, G. Sotgiu, M. Colapietro, and A. Inesi Diastereoselective Electrochemical Carboxylation of Chiral α- Bromocarboxylic Acid Derivatives: An Easy Access to Unsymmetrical Alkylmalonic Ester Derivatives J. Org. Chem. 69 2004 487
    • (2004) J. Org. Chem. , vol.69 , pp. 487
    • Feroci, M.1    Orsini, M.2    Palombi, L.3    Sotgiu, G.4    Colapietro, M.5    Inesi, A.6
  • 32
    • 84890309771 scopus 로고
    • The electrochemistry of the C = C, C = O and C = N groups
    • S. Patai, John Wiley & Sons New York
    • A.J. Fry The electrochemistry of the C = C, C = O and C = N groups S. Patai, Synthetic Organic Electrochemistry, Ch. 12 1989 John Wiley & Sons New York 1 3
    • (1989) Synthetic Organic Electrochemistry, Ch. 12 , pp. 1-3
    • Fry, A.J.1
  • 33
    • 0037453363 scopus 로고    scopus 로고
    • Enantioselective cathodic reduction of some prochiral ketones in the presence of (-)-N,N'-dimethylquininium tetrafluoroborate at mercury cathode
    • A.K. Yadav, M. Manju, and P.R. Chhinpa Enantioselective cathodic reduction of some prochiral ketones in the presence of (-)-N,N'- dimethylquininium tetrafluoroborate at mercury cathode Tetrahedron: Asymmetry 14 2003 1079
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 1079
    • Yadav, A.K.1    Manju, M.2    Chhinpa, P.R.3
  • 34
    • 35549013712 scopus 로고    scopus 로고
    • Enantioselective electrocatalytic hydrogenation of ethyl pyruvate on carbon supported Pd electrodes
    • M. Vago, F.J. Williams, and E.J. Calvo Enantioselective electrocatalytic hydrogenation of ethyl pyruvate on carbon supported Pd electrodes Electrochem. Commun. 9 2007 2725
    • (2007) Electrochem. Commun. , vol.9 , pp. 2725
    • Vago, M.1    Williams, F.J.2    Calvo, E.J.3
  • 35
    • 84986646089 scopus 로고
    • Enantioselective Cathodic Reduction of 4-Substituted Coumarins with Alkaloids as Catalysts
    • N. Schoo, and H.-J. Schafer Enantioselective Cathodic Reduction of 4-Substituted Coumarins with Alkaloids as Catalysts 1, J. Liebigs Ann. Chem. 1993 601
    • (1993) 1, J. Liebigs Ann. Chem. , pp. 601
    • Schoo, N.1    Schafer, H.-J.2
  • 36
    • 0043192678 scopus 로고    scopus 로고
    • Electrochemical Carboxylation of N-(2-Bromopropionyl)-4Rphenyloxazolidin- 2-one: An Efficient Route to Unsymmetrical Methylmalonic Ester Derivatives
    • M. Feroci, A. Inesi, M. Orsini, and L. Palombi Electrochemical Carboxylation of N-(2-Bromopropionyl)-4Rphenyloxazolidin-2-one: An Efficient Route to Unsymmetrical Methylmalonic Ester Derivatives Org. Lett. 4 2002 2617
    • (2002) Org. Lett. , vol.4 , pp. 2617
    • Feroci, M.1    Inesi, A.2    Orsini, M.3    Palombi, L.4
  • 37
    • 17544381858 scopus 로고    scopus 로고
    • Stereoselective electrochemical carboxylation: 2-phenylsuccinates from chiral cinnamic acid derivatives
    • M. Orsini, M. Feroci, G. Sotgiub, and A. Inesi Stereoselective electrochemical carboxylation: 2-phenylsuccinates from chiral cinnamic acid derivatives Org. Biomol. Chem. 3 2005 1202
    • (2005) Org. Biomol. Chem. , vol.3 , pp. 1202
    • Orsini, M.1    Feroci, M.2    Sotgiub, G.3    Inesi, A.4
  • 38
    • 64549130810 scopus 로고    scopus 로고
    • Asymmetric electrochemical carboxylation of prochiral acetophenone: An efficient route to optically active atrolactic acid via selective fixation of carbon dioxide
    • K. Zhang, H. Wang, S.-F. Zhao, D.-F. Niu, and J.-X. Lu Asymmetric electrochemical carboxylation of prochiral acetophenone: An efficient route to optically active atrolactic acid via selective fixation of carbon dioxide J. Electroanaly. Chem. 630 2009 35
    • (2009) J. Electroanaly. Chem. , vol.630 , pp. 35
    • Zhang, K.1    Wang, H.2    Zhao, S.-F.3    Niu, D.-F.4    Lu, J.-X.5
  • 39
    • 79955478769 scopus 로고    scopus 로고
    • Alkaloid induced asymmetric electrocarboxylation of 4-methylpropiophenone
    • S.-F. Zhao, M.-X. Zhu, K. Zhang, H. Wang, and J.-X. Lu Alkaloid induced asymmetric electrocarboxylation of 4-methylpropiophenone Tetrahedron Lett. 52 2011 2702
    • (2011) Tetrahedron Lett. , vol.52 , pp. 2702
    • Zhao, S.-F.1    Zhu, M.-X.2    Zhang, K.3    Wang, H.4    Lu, J.-X.5
  • 43
    • 0000456247 scopus 로고
    • A Novel Synthesis of 2-Aryllactic Acids via Electrocarboxylation of Methyl Aryl Ketones
    • A.S.C. Chan, T.T. Huang, J.H. Wagenknecht, and R.E. Miller A Novel Synthesis of 2-Aryllactic Acids via Electrocarboxylation of Methyl Aryl Ketones J. Org. Chem. 60 1995 742
    • (1995) J. Org. Chem. , vol.60 , pp. 742
    • Chan, A.S.C.1    Huang, T.T.2    Wagenknecht, J.H.3    Miller, R.E.4
  • 44
    • 0000278312 scopus 로고
    • The role of quinidine in induction of asymmetric synthesis at mercury cathodes
    • E. Kariv, H.A. Terni, and E. Gileadi The role of quinidine in induction of asymmetric synthesis at mercury cathodes Electrochim. Acta 18 1973 433
    • (1973) Electrochim. Acta , vol.18 , pp. 433
    • Kariv, E.1    Terni, H.A.2    Gileadi, E.3
  • 45
    • 77954529000 scopus 로고    scopus 로고
    • Efficient Electrocarboxylation of p-Methylpropiophenone in the Presence of Carbon Dioxide
    • K. Zhang, H. Wang, L.-X. Wu, J.-B. Zhang, and J.-X. Lu Efficient Electrocarboxylation of p-Methylpropiophenone in the Presence of Carbon Dioxide Chin. J. Chem. 28 2010 509
    • (2010) Chin. J. Chem. , vol.28 , pp. 509
    • Zhang, K.1    Wang, H.2    Wu, L.-X.3    Zhang, J.-B.4    Lu, J.-X.5
  • 46
    • 0002425619 scopus 로고    scopus 로고
    • Heterogeneous enantioselective hydrogenation of trifluoromethyl ketones
    • D.C. Sherrington, A.P. Kybett, Royal Soc. Chem. Special Publication Cambridge
    • V.M. Arx, T. Mallat, and A. Baiker Heterogeneous enantioselective hydrogenation of trifluoromethyl ketones D.C. Sherrington, A.P. Kybett, Supported Reagents and their Applications 2001 Royal Soc. Chem. Special Publication Cambridge 247 254
    • (2001) Supported Reagents and Their Applications , pp. 247-254
    • Arx, V.M.1    Mallat, T.2    Baiker, A.3
  • 47
    • 0035842865 scopus 로고    scopus 로고
    • Platinum-catalyzed enantioselective hydrogenation of aryl-substituted trifluoroacetophenones
    • M.V. Arx, T. Mallat, and A. Baiker Platinum-catalyzed enantioselective hydrogenation of aryl-substituted trifluoroacetophenones Tetrahedron: Asymmetry 12 2001 3089
    • (2001) Tetrahedron: Asymmetry , vol.12 , pp. 3089
    • Arx, M.V.1    Mallat, T.2    Baiker, A.3
  • 48
    • 0001462332 scopus 로고    scopus 로고
    • Enantioselective Hydrogenation of α,β-Unsaturated Carboxylic Acids over Cinchonidine Modified Palladium: Nature of Modifier-Reactant Interaction
    • K. Borszeky, T. Burgi, Z. Zhaohui, T. Mallat, and A. Baiker Enantioselective Hydrogenation of α,β-Unsaturated Carboxylic Acids over Cinchonidine Modified Palladium: Nature of Modifier-Reactant Interaction J. Catal. 187 1999 160
    • (1999) J. Catal. , vol.187 , pp. 160
    • Borszeky, K.1    Burgi, T.2    Zhaohui, Z.3    Mallat, T.4    Baiker, A.5
  • 49
    • 2542456591 scopus 로고    scopus 로고
    • Heterogeneous asymmetric reactions Part 38. Enantioselective hydrogenation of fluoroketones on Pt-alumina catalyst
    • T. Varga, K. Felföldi, P. Forgó, and M. Bartók Heterogeneous asymmetric reactions Part 38. Enantioselective hydrogenation of fluoroketones on Pt-alumina catalyst J. Mol. Catal. A: Chem. 216 2004 181
    • (2004) J. Mol. Catal. A: Chem. , vol.216 , pp. 181
    • Varga, T.1    Felföldi, K.2    Forgó, P.3    Bartók, M.4
  • 50
    • 0037087655 scopus 로고    scopus 로고
    • Enantioselective Hydrogenation over Cinchona-Modified Pt: The Special Role of Carboxylic Acids
    • M.V. Arx, T. Burgi, T. Mallat, and A. Baiker Enantioselective Hydrogenation over Cinchona-Modified Pt: The Special Role of Carboxylic Acids Chem. Eur. J. 8 2002 1430
    • (2002) Chem. Eur. J. , vol.8 , pp. 1430
    • Arx, M.V.1    Burgi, T.2    Mallat, T.3    Baiker, A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.