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Volumn 89, Issue , 2013, Pages 692-699

Internal redox amidation of α,β-unsaturated aldehydes in ionic liquids. The electrochemical route

Author keywords

Amides; N Heterocyclic carbenes; Organic electrosynthesis; Room temperature ionic liquids; , Unsaturated aldehydes

Indexed keywords

ALDEHYDES; AMIDES; MOLAR RATIO; ORGANIC SOLVENTS; SYNTHESIS (CHEMICAL);

EID: 84871576637     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.electacta.2012.11.061     Document Type: Article
Times cited : (17)

References (51)
  • 1
    • 26844576835 scopus 로고    scopus 로고
    • Amide bond formation and peptide coupling
    • C.A.G.N. Montalbetti, and V. Falque Amide bond formation and peptide coupling Tetrahedron 61 2005 10827
    • (2005) Tetrahedron , vol.61 , pp. 10827
    • Montalbetti, C.A.G.N.1    Falque, V.2
  • 2
    • 62449152302 scopus 로고    scopus 로고
    • Amide bond formation: Beyond the myth of coupling reagents
    • E. Valeur, and M. Bradley Amide bond formation: beyond the myth of coupling reagents Chemical Society Reviews 38 2009 606
    • (2009) Chemical Society Reviews , vol.38 , pp. 606
    • Valeur, E.1    Bradley, M.2
  • 3
  • 4
    • 84860207609 scopus 로고    scopus 로고
    • Dual Brønsted acid/nucleophilic activation of carbonylimidazole derivatives
    • S.T. Heller, T. Fu, and R. Sarpong Dual Brønsted acid/nucleophilic activation of carbonylimidazole derivatives Organic Letters 14 2012 1970
    • (2012) Organic Letters , vol.14 , pp. 1970
    • Heller, S.T.1    Fu, T.2    Sarpong, R.3
  • 5
    • 84862010010 scopus 로고    scopus 로고
    • The phosphate-carboxylate mixed-anhydride method: A mild, efficient process for ester and amide bond construction
    • J. McNulty, R. Vemula, V. Krishnamoorthy, and A. Robertson The phosphate-carboxylate mixed-anhydride method: A mild, efficient process for ester and amide bond construction Tetrahedron 68 2012 5415
    • (2012) Tetrahedron , vol.68 , pp. 5415
    • Mcnulty, J.1    Vemula, R.2    Krishnamoorthy, V.3    Robertson, A.4
  • 7
    • 0027258043 scopus 로고
    • A simple preparation of amides from acids and amines by heating of their mixture
    • B.S. Jursic, and Z. Zdravkovski A simple preparation of amides from acids and amines by heating of their mixture Synthetic Communications 23 1993 2761
    • (1993) Synthetic Communications , vol.23 , pp. 2761
    • Jursic, B.S.1    Zdravkovski, Z.2
  • 8
    • 79959403001 scopus 로고    scopus 로고
    • Metal-catalysed approaches to amide bond formation
    • C.L. Allen, and J.M.J. Williams Metal-catalysed approaches to amide bond formation Chemical Society Reviews 40 2011 3405
    • (2011) Chemical Society Reviews , vol.40 , pp. 3405
    • Allen, C.L.1    Williams, J.M.J.2
  • 9
    • 33746908959 scopus 로고    scopus 로고
    • Enantioselective biotransformations of nitriles in organic synthesis
    • M.X. Wang Enantioselective biotransformations of nitriles in organic synthesis Topics in Catalysis 35 2005 117
    • (2005) Topics in Catalysis , vol.35 , pp. 117
    • Wang, M.X.1
  • 11
    • 83455245722 scopus 로고    scopus 로고
    • Direct amide formation from unactivated carboxylic acids and amines
    • C.L. Allen, A.R. Chhatwal, and J.M.J. Williams Direct amide formation from unactivated carboxylic acids and amines Chemical Communications 48 2012 666
    • (2012) Chemical Communications , vol.48 , pp. 666
    • Allen, C.L.1    Chhatwal, A.R.2    Williams, J.M.J.3
  • 12
    • 84858966064 scopus 로고    scopus 로고
    • Direct amide coupling of non-activated carboxylic acids and amines catalysed by zirconium(IV) chloride
    • H. Lundberg, F. Tinnis, and H. Adolfsson Direct amide coupling of non-activated carboxylic acids and amines catalysed by zirconium(IV) chloride Chemistry- A European Journal 18 2012 3822
    • (2012) Chemistry- A European Journal , vol.18 , pp. 3822
    • Lundberg, H.1    Tinnis, F.2    Adolfsson, H.3
  • 14
    • 34250862807 scopus 로고    scopus 로고
    • Key green chemistry research areas - A perspective from pharmaceutical manufacturers
    • D.J.C. Constable Key green chemistry research areas - a perspective from pharmaceutical manufacturers Green Chemistry 9 2007 411
    • (2007) Green Chemistry , vol.9 , pp. 411
    • Constable, D.J.C.1
  • 15
    • 84255197846 scopus 로고    scopus 로고
    • Rethinking amide bond synthesis
    • V.R. Pattabiraman, and J.W. Bode Rethinking amide bond synthesis Nature 480 2011 471
    • (2011) Nature , vol.480 , pp. 471
    • Pattabiraman, V.R.1    Bode, J.W.2
  • 16
    • 77953930529 scopus 로고    scopus 로고
    • Amide bonds made in reverse
    • K. Scheidt Amide bonds made in reverse Nature 465 2010 1020
    • (2010) Nature , vol.465 , pp. 1020
    • Scheidt, K.1
  • 17
    • 68949131249 scopus 로고    scopus 로고
    • Beyond conventional N-heterocyclic carbenes: Abnormal, remote, and other classes of NHC ligands with reduced heteroatom stabilization
    • O. Schuster, L. Yang, H.G. Raubenheimer, and M. Albrecht Beyond conventional N-heterocyclic carbenes: abnormal, remote, and other classes of NHC ligands with reduced heteroatom stabilization Chemical Reviews 109 2009 3445
    • (2009) Chemical Reviews , vol.109 , pp. 3445
    • Schuster, O.1    Yang, L.2    Raubenheimer, H.G.3    Albrecht, M.4
  • 18
    • 75649103176 scopus 로고    scopus 로고
    • Percent buries volume for phosphine and N-heterocyclic carbene ligands: Steric properties in organometallic chemistry
    • H. Clavier, and S.P. Nolan Percent buries volume for phosphine and N-heterocyclic carbene ligands: steric properties in organometallic chemistry Chemical Communications 46 2010 841
    • (2010) Chemical Communications , vol.46 , pp. 841
    • Clavier, H.1    Nolan, S.P.2
  • 20
    • 84859747983 scopus 로고    scopus 로고
    • Organocatalytic umpolung: N-heterocyclic carbenes and beyond
    • X. Bugaut, and F. Glorius Organocatalytic umpolung: N-heterocyclic carbenes and beyond Chemical Society Reviews 41 2012 3511
    • (2012) Chemical Society Reviews , vol.41 , pp. 3511
    • Bugaut, X.1    Glorius, F.2
  • 21
    • 82355163624 scopus 로고    scopus 로고
    • Chemoselective conversion of α-unbranched aldehydes to amides, esters, and carboxylic acids by NHC-catalysis
    • S. Kuwano, S. Harada, R. Oriez, and K.-I. Yamada Chemoselective conversion of α-unbranched aldehydes to amides, esters, and carboxylic acids by NHC-catalysis Chemical Communications 48 2012 145
    • (2012) Chemical Communications , vol.48 , pp. 145
    • Kuwano, S.1    Harada, S.2    Oriez, R.3    Yamada, K.-I.4
  • 22
    • 79959990563 scopus 로고    scopus 로고
    • Oxidative esterification, thioesterification, and amidation of aldehydes by a two-component organocatalytic system using a chiral N-heterocyclic carbene and redox-active riboflavin
    • S. Iwahana, H. Iida, and E. Yashima Oxidative esterification, thioesterification, and amidation of aldehydes by a two-component organocatalytic system using a chiral N-heterocyclic carbene and redox-active riboflavin Chemistry- A European Journal 17 2011 8009
    • (2011) Chemistry- A European Journal , vol.17 , pp. 8009
    • Iwahana, S.1    Iida, H.2    Yashima, E.3
  • 23
    • 53849129886 scopus 로고    scopus 로고
    • One-pot oxidative esterification and amidation of aldehydes
    • K. Ekoue-Kovi, and C. Wolf One-pot oxidative esterification and amidation of aldehydes Chemistry- A European Journal 14 2008 6302
    • (2008) Chemistry- A European Journal , vol.14 , pp. 6302
    • Ekoue-Kovi, K.1    Wolf, C.2
  • 24
    • 15244343088 scopus 로고    scopus 로고
    • Conversion of α,β-unsaturated aldehydes into saturated esters: An umpolung reaction catalyzed by nucleophilic carbenes
    • A. Chan, and K.A. Scheidt Conversion of α,β-unsaturated aldehydes into saturated esters: an umpolung reaction catalyzed by nucleophilic carbenes Organic Letters 7 2005 905
    • (2005) Organic Letters , vol.7 , pp. 905
    • Chan, A.1    Scheidt, K.A.2
  • 25
    • 24944439544 scopus 로고    scopus 로고
    • Catalytic generation of activated carboxylated from enals: A product-determining role for the base
    • S.S. Sohn, and J.W. Bode Catalytic generation of activated carboxylated from enals: A product-determining role for the base Organic Letters 7 2005 3873
    • (2005) Organic Letters , vol.7 , pp. 3873
    • Sohn, S.S.1    Bode, J.W.2
  • 26
    • 33644764723 scopus 로고    scopus 로고
    • Stereoselective synthesis of (E)-α,β-unsaturated esters via carbene-catalyzed redox esterification
    • K. Zeitler Stereoselective synthesis of (E)-α,β-unsaturated esters via carbene-catalyzed redox esterification Organic Letters 8 2006 637
    • (2006) Organic Letters , vol.8 , pp. 637
    • Zeitler, K.1
  • 27
    • 3543074145 scopus 로고    scopus 로고
    • Conversion of α-haloaldehydes into acylating agents by an internal redox reaction catalyzed by nucleophilic carbenes
    • N.T. Reynolds, J.R. de Alaniz, and T. Rovis Conversion of α-haloaldehydes into acylating agents by an internal redox reaction catalyzed by nucleophilic carbenes Journal of the American Chemical Society 126 2004 9518
    • (2004) Journal of the American Chemical Society , vol.126 , pp. 9518
    • Reynolds, N.T.1    De Alaniz, J.R.2    Rovis, T.3
  • 28
    • 28444444128 scopus 로고    scopus 로고
    • Enantioselective protonation of catalytically generated chiral enolates as an approach to the synthesis of α-chloro esters
    • N.T. Reynolds, and T. Rovis Enantioselective protonation of catalytically generated chiral enolates as an approach to the synthesis of α-chloro esters Journal of the American Chemical Society 127 2005 16406
    • (2005) Journal of the American Chemical Society , vol.127 , pp. 16406
    • Reynolds, N.T.1    Rovis, T.2
  • 29
    • 36149000925 scopus 로고    scopus 로고
    • Nucleophilic carbene and HOAt relay catalysis in an amide bond coupling: An orthogonal peptide bond forming reaction
    • H.U. Vora, and T. Rovis Nucleophilic carbene and HOAt relay catalysis in an amide bond coupling: an orthogonal peptide bond forming reaction Journal of the American Chemical Society 129 2007 13796
    • (2007) Journal of the American Chemical Society , vol.129 , pp. 13796
    • Vora, H.U.1    Rovis, T.2
  • 30
    • 36148946729 scopus 로고    scopus 로고
    • N-heterocyclic carbene-catalyzed redox amidations of α- functionalized aldehydes with amines
    • J.W. Bode, and S.S. Sohn N-heterocyclic carbene-catalyzed redox amidations of α-functionalized aldehydes with amines Journal of the American Chemical Society 129 2007 13798
    • (2007) Journal of the American Chemical Society , vol.129 , pp. 13798
    • Bode, J.W.1    Sohn, S.S.2
  • 31
    • 68149144341 scopus 로고    scopus 로고
    • Catalytic amide formation with α′-hydroxyenones as acylating reagents
    • P.-C. Chiang, Y. Kim, and J.W. Bode Catalytic amide formation with α′-hydroxyenones as acylating reagents Chemical Communications 45 2009 4566
    • (2009) Chemical Communications , vol.45 , pp. 4566
    • Chiang, P.-C.1    Kim, Y.2    Bode, J.W.3
  • 32
    • 50249101313 scopus 로고    scopus 로고
    • Reactivity of electrogenerated N-heterocyclic carbene in room-temperature ionic liquids. Cyclization to 2-azetidinone ring via C3-C4 bond formation
    • M. Feroci, I. Chiarotto, M. Orsini, G. Sotgiu, and A. Inesi Reactivity of electrogenerated N-heterocyclic carbene in room-temperature ionic liquids. Cyclization to 2-azetidinone ring via C3-C4 bond formation Advanced Synthesis and Catalysis 350 2008 1355
    • (2008) Advanced Synthesis and Catalysis , vol.350 , pp. 1355
    • Feroci, M.1    Chiarotto, I.2    Orsini, M.3    Sotgiu, G.4    Inesi, A.5
  • 33
    • 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
  • 34
    • 63049111179 scopus 로고    scopus 로고
    • Electrogenerated N-heterocyclic carbene. N-Functionalization of benzoxazolones
    • I. Chiarotto, M. Feroci, M. Orsini, G. Sotgiu, and A. Inesi Electrogenerated N-heterocyclic carbene. N-Functionalization of benzoxazolones Tetrahedron 65 2009 3704
    • (2009) Tetrahedron , vol.65 , pp. 3704
    • Chiarotto, I.1    Feroci, M.2    Orsini, M.3    Sotgiu, G.4    Inesi, A.5
  • 35
    • 67649486829 scopus 로고    scopus 로고
    • The double role of ionic liquids in organic electrosynthesis: Precursors of N-heterocyclic carbenes and green solvents. Henry reaction
    • M. Feroci, M.N. Elinson, L. Rossi, and A. Inesi The double role of ionic liquids in organic electrosynthesis: precursors of N-heterocyclic carbenes and green solvents. Henry reaction Electrochemistry Communications 11 2009 1523
    • (2009) Electrochemistry Communications , vol.11 , pp. 1523
    • Feroci, M.1    Elinson, M.N.2    Rossi, L.3    Inesi, A.4
  • 36
    • 77953194224 scopus 로고    scopus 로고
    • Electrogenerated NHC as an organocatalyst in the Staudinger reaction
    • M. Feroci, I. Chiarotto, M. Orsini, and A. Inesi Electrogenerated NHC as an organocatalyst in the Staudinger reaction Chemical Communications 46 2010 4121
    • (2010) Chemical Communications , vol.46 , pp. 4121
    • Feroci, M.1    Chiarotto, I.2    Orsini, M.3    Inesi, A.4
  • 37
    • 79958108187 scopus 로고    scopus 로고
    • Umpolung of α,β-unsaturated aldehydes by electrogenerated NHCs in ionic liquids: Synthesis of γ-butyrolactones
    • M. Orsini, I. Chiarotto, M.M.M. Feeney, M. Feroci, G. Sotgiu, and A. Inesi Umpolung of α,β-unsaturated aldehydes by electrogenerated NHCs in ionic liquids: synthesis of γ-butyrolactones Electrochemistry Communications 13 2011 738
    • (2011) Electrochemistry Communications , vol.13 , pp. 738
    • Orsini, M.1    Chiarotto, I.2    Feeney, M.M.M.3    Feroci, M.4    Sotgiu, G.5    Inesi, A.6
  • 38
    • 84866139041 scopus 로고    scopus 로고
    • Investigation of the role of electrogenerated N-heterocyclic carbene in the staudinger synthesis in ionic liquid
    • M. Feroci Investigation of the role of electrogenerated N-heterocyclic carbene in the staudinger synthesis in ionic liquid International Journal of Organic Chemistry 1 2011 191
    • (2011) International Journal of Organic Chemistry , vol.1 , pp. 191
    • Feroci, M.1
  • 39
    • 84860830829 scopus 로고    scopus 로고
    • Umpolung reactions in ionic liquid catalyzed by electrogenerated N-heterocyclic carbenes. Synthesis of saturated esters from activated α,β-unsaturated aldehydes
    • M. Feroci, I. Chiarotto, M. Orsini, R. Pelagalli, and A. Inesi Umpolung reactions in ionic liquid catalyzed by electrogenerated N-heterocyclic carbenes. Synthesis of saturated esters from activated α,β-unsaturated aldehydes Chemical Communications 48 2012 5361
    • (2012) Chemical Communications , vol.48 , pp. 5361
    • Feroci, M.1    Chiarotto, I.2    Orsini, M.3    Pelagalli, R.4    Inesi, A.5
  • 40
    • 41449111035 scopus 로고    scopus 로고
    • Synthesis of dihydropyridines and pyridines from imines and alkynes via C-H activation
    • D.A. Colby, R.G. Bergman, and J.A. Ellman Synthesis of dihydropyridines and pyridines from imines and alkynes via C-H activation Journal of the American Chemical Society 130 2008 3645
    • (2008) Journal of the American Chemical Society , vol.130 , pp. 3645
    • Colby, D.A.1    Bergman, R.G.2    Ellman, J.A.3
  • 42
    • 2142715902 scopus 로고    scopus 로고
    • The effective use of substituted benzoic anhydrides for the synthesis of carboxamides
    • I. Shiina, and Y. Kawakita The effective use of substituted benzoic anhydrides for the synthesis of carboxamides Tetrahedron 60 2004 4729
    • (2004) Tetrahedron , vol.60 , pp. 4729
    • Shiina, I.1    Kawakita, Y.2
  • 43
    • 0030575364 scopus 로고    scopus 로고
    • N-hydroxypyridine-2(1H)-thione derivatives of carboxylic acids as activated esters. Part I. The synthesis of carboxamides
    • D.H.R. Barton, and J.A. Ferreira N-hydroxypyridine-2(1H)-thione derivatives of carboxylic acids as activated esters. Part I. The synthesis of carboxamides Tetrahedron 52 1996 9347
    • (1996) Tetrahedron , vol.52 , pp. 9347
    • Barton, D.H.R.1    Ferreira, J.A.2
  • 44
    • 0001430851 scopus 로고    scopus 로고
    • Development of a reductive alkylation method using p-Benzyloxybenzylamine (BOBA) resin for the synthesis of N-alkylated amides
    • Y. Aoki, and S. Kobayashi Development of a reductive alkylation method using p-Benzyloxybenzylamine (BOBA) resin for the synthesis of N-alkylated amides Journal of Combinatorial Chemistry 1 1999 371
    • (1999) Journal of Combinatorial Chemistry , vol.1 , pp. 371
    • Aoki, Y.1    Kobayashi, S.2
  • 45
    • 78449290409 scopus 로고    scopus 로고
    • Catalytic acylation of amines with aldehydes or aldoximes
    • C.L. Allen, S. Davulcu, and M.J. Williams Catalytic acylation of amines with aldehydes or aldoximes Organic Letters 12 2010 5096
    • (2010) Organic Letters , vol.12 , pp. 5096
    • Allen, C.L.1    Davulcu, S.2    Williams, M.J.3
  • 48
    • 70349413087 scopus 로고    scopus 로고
    • Although this particular NHC has never been isolated, in previous works we have trapped it by reaction with sulfur, to give the corresponding imidazole-2-thione
    • and with aliphatic aldehydes, to yield the corresponding ionic adducts (I. Chiarotto, M., Feroci, M., Orsini, M. M. M. Feeney, A., Inesi, Advanced Synthesis & Catalysis 352 (2010) 3287)
    • Although this particular NHC has never been isolated, in previous works we have trapped it by reaction with sulfur, to give the corresponding imidazole-2-thione (M. Feroci, M., Orsini, A., Inesi, Adv. Synth. Catal. 351 (2009) 2067) and with aliphatic aldehydes, to yield the corresponding ionic adducts (I. Chiarotto, M., Feroci, M., Orsini, M. M. M. Feeney, A., Inesi, Advanced Synthesis & Catalysis 352 (2010) 3287).
    • (2009) Adv. Synth. Catal. , vol.351 , pp. 2067
    • Feroci, M.1    Orsini, M.2    Inesi, A.3
  • 50
    • 77749236922 scopus 로고    scopus 로고
    • Polarity reversal induced by electrochemically generated thiazol-2-ylidenes: The Stetter reaction
    • M. Orsini, I. Chiarotto, G. Sotgiu, and A. Inesi Polarity reversal induced by electrochemically generated thiazol-2-ylidenes: the Stetter reaction Electrochimica Acta 55 2010 5823
    • (2010) Electrochimica Acta , vol.55 , pp. 5823
    • Orsini, M.1    Chiarotto, I.2    Sotgiu, G.3    Inesi, A.4


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