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Volumn 40, Issue 2, 2010, Pages 179-185

Nickel-catalyzed alkynylation of aryl iodides (Sonogashira Reaction) in water

Author keywords

Alkynylation; Aryl iodide; Nickel catalyst; Sonogashira reaction

Indexed keywords

ACETYLENE DERIVATIVE; ALKYNE; ALKYNYL GROUP; CARBONIC ACID; CESIUM; COPPER; DODECYLSULFATE AMMONIUM; IODIDE; NICKEL; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SURFACTANT;

EID: 73949140681     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802630187     Document Type: Article
Times cited : (30)

References (36)
  • 1
    • 9644285669 scopus 로고
    • A convenient synthesis of acetylenes: Catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes, and bromopyridines
    • Sonogashira, K.; Tohda, Y.; Hagihara, N. A convenient synthesis of acetylenes: Catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes, and bromopyridines. Tetrahedron Lett. 1975, 16, 4467-4470.
    • (1975) Tetrahedron Lett. , vol.16 , pp. 4467-4470
    • Sonogashira, K.1    Tohda, Y.2    Hagihara, N.3
  • 2
    • 0000963686 scopus 로고    scopus 로고
    • Shape-persistent molecular architectures of nanoscale dimension
    • Moore, J. S. Shape-persistent molecular architectures of nanoscale dimension. Acc. Chem. Res. 1997, 30, 402-413.
    • (1997) Acc. Chem. Res. , vol.30 , pp. 402-413
    • Moore, J.S.1
  • 4
    • 0037943974 scopus 로고    scopus 로고
    • Palladium-catalyzed alkynylation
    • Negishi, E.-J.; Anastasia, L. Palladium-catalyzed alkynylation. Chem. Rev. 2003, 103, 1979-2018.
    • (2003) Chem. Rev. , vol.103 , pp. 1979-2018
    • Negishi, E.-J.1    Anastasia, L.2
  • 5
    • 0035831163 scopus 로고    scopus 로고
    • A highly selective synthesis of diarylethynes and their oligomers by a palladium-catalyzed Sonogashira coupling reaction under phase transfer conditions
    • Chow, H.-F.; Wan, C.-W.; Low, K.-H.; Yeung, Y.-Y. A highly selective synthesis of diarylethynes and their oligomers by a palladium-catalyzed Sonogashira coupling reaction under phase transfer conditions. J. Org. Chem. 2001, 66, 1910-1913.
    • (2001) J. Org. Chem. , vol.66 , pp. 1910-1913
    • Chow, H.-F.1    Wan, C.-W.2    Low, K.-H.3    Yeung, Y.-Y.4
  • 6
    • 0035833686 scopus 로고    scopus 로고
    • Chemoselective Pd(0)-catalyzed peptide coupling in water
    • (a) Bong, D. T.; Ghadiri, M. R. Chemoselective Pd(0)-catalyzed peptide coupling in water. Org. Lett. 2001, 3, 2509-2511;
    • (2001) Org. Lett. , Issue.3 , pp. 2509-2511
    • Bong, D.T.1    Ghadiri, M.R.2
  • 7
    • 0032510011 scopus 로고    scopus 로고
    • Sonogashira cross-couplings using biocompatible conditions in water
    • (b) Dibowski, H.; Schmidtchen, F. P. Sonogashira cross-couplings using biocompatible conditions in water. Tetrahedron Lett. 1998, 39, 525-528;
    • (1998) Tetrahedron Lett. , vol.39 , pp. 525-528
    • Dibowski, H.1    Schmidtchen, F.P.2
  • 8
    • 0007512358 scopus 로고
    • Palladium-catalyzed alkylations in aqueous media
    • (c) Casalnuovo, A. L.; Calabrese, J. C. Palladium-catalyzed alkylations in aqueous media. J. Am. Chem. Soc. 1990, 112, 4324-4330.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 4324-4330
    • Casalnuovo, A.L.1    Calabrese, J.C.2
  • 9
    • 0034235216 scopus 로고    scopus 로고
    • Rapid microwave-enhanced, solventless Sonogashira coupling reaction on alumina
    • Kabalka, G. W.; Wang, L.; Namboodiri, V.; Pagni, R. M. Rapid microwave-enhanced, solventless Sonogashira coupling reaction on alumina. Tetrahedron Lett. 2000, 41, 5151-5154.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 5151-5154
    • Kabalka, G.W.1    Wang, L.2    Namboodiri, V.3    Pagni, R.M.4
  • 10
    • 0030605876 scopus 로고    scopus 로고
    • An efficient palladium-catalysed coupling of terminal alkynes with aryl halides under Jeffery's conditions
    • (a) Nguefack, J.-F.; Bolitt, V.; Sinou, D. An efficient palladium-catalysed coupling of terminal alkynes with aryl halides under Jeffery's conditions. Tetrahedron Lett. 1996, 37, 5527-5530;
    • (1996) Tetrahedron Lett. , vol.37 , pp. 5527-5530
    • Nguefack, J.-F.1    Bolitt, V.2    Sinou, D.3
  • 11
    • 0002598702 scopus 로고    scopus 로고
    • Bis(pyrimidine)-based palladium catalysts: Synthesis, X-ray structure, and applications in Heck-, Suzuki-, Sonogashira-Hagihara couplings and amination reactions
    • (b) Buchmeiser, M. R.; Schareina, T.; Kempe, R.; Wurst, K. Bis(pyrimidine)-based palladium catalysts: Synthesis, X-ray structure, and applications in Heck-, Suzuki-, Sonogashira-Hagihara couplings and amination reactions. J. Organomet. Chem. 2001, 634, 39-46;
    • (2001) J. Organomet. Chem. , vol.634 , pp. 39-46
    • Buchmeiser, M.R.1    Schareina, T.2    Kempe, R.3    Wurst, K.4
  • 12
    • 0033678083 scopus 로고    scopus 로고
    • Coordination chemistry and mechanisms of metal-catalyzed C-C coupling reactions 13: A copper-free procedure for the palladium-catalyzed Sonogashira reaction of aryl bromides with terminal alkynes at room temperature
    • (c) Bohm, V. P. W.; Herrmann, W. A. Coordination chemistry and mechanisms of metal-catalyzed C-C coupling reactions, 13: A copper-free procedure for the palladium-catalyzed Sonogashira reaction of aryl bromides with terminal alkynes at room temperature. Eur. J. Org. Chem. 2000, 65, 3679-3681;
    • (2000) Eur. J. Org. Chem. , vol.65 , pp. 3679-3681
    • Bohm, V.P.W.1    Herrmann, W.A.2
  • 13
    • 0034658926 scopus 로고    scopus 로고
    • 3: A versatile catalyst for Sonogashira reactions of aryl bromides at room temperature
    • 3: A versatile catalyst for Sonogashira reactions of aryl bromides at room temperature. Org. Lett. 2000, 2, 1729-1731;
    • (2000) Org. Lett. , vol.2 , pp. 1729-1731
    • Hundertmark, T.1    Littke, A.F.2    Buchwald, S.L.3    Fu, G.C.4
  • 14
    • 0035961019 scopus 로고    scopus 로고
    • Air-stable trialkylphosphonium salts: Simple, practical, and versatile replacements for air-sensitive trialkylphosphines: Applications in stoichio-metric and catalytic processes
    • (e) Netherton, M. R.; Fu, G. C. Air-stable trialkylphosphonium salts: Simple, practical, and versatile replacements for air-sensitive trialkylphosphines: Applications in stoichio-metric and catalytic processes. Org. Lett. 2001, 3, 4295-4297.
    • (2001) Org. Lett. , vol.3 , pp. 4295-4297
    • Netherton, M.R.1    Fu, G.C.2
  • 15
    • 0001036626 scopus 로고    scopus 로고
    • Palladium-catalysed coupling of terminal alkynes with aryl halides aided by catalytic zinc
    • (a) Crisp, G. T.; Turner, P. D.; Stephens, K. A. Palladium-catalysed coupling of terminal alkynes with aryl halides aided by catalytic zinc. J. Organomet. Chem. 1998, 570, 219-224;
    • (1998) J. Organomet. Chem. , vol.570 , pp. 219-224
    • Crisp, G.T.1    Turner, P.D.2    Stephens, K.A.3
  • 16
    • 0030605058 scopus 로고    scopus 로고
    • Iodide acceleration in the Pd-catalyzed coupling of aromatic 1,2-ditriflates with alkynes: Synthesis of enediynes
    • (b) Powell, N. A.; Rychnovsky, S. D. Iodide acceleration in the Pd-catalyzed coupling of aromatic 1,2-ditriflates with alkynes: Synthesis of enediynes. Tetrahedron Lett. 1996, 37, 7901-7904;
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7901-7904
    • Powell, N.A.1    Rychnovsky, S.D.2
  • 17
    • 0035974363 scopus 로고    scopus 로고
    • Chemistry of aminophenols, part 1: Remarkable additive effect on Sonogashira cross-coupling of 2-carboxamidoaryl triflates and application to novel synthesis of indoles
    • (c) Dai, W.-M.; Guo, D.-S.; Sun, L.-P. Chemistry of aminophenols, part 1: Remarkable additive effect on Sonogashira cross-coupling of 2-carboxamidoaryl triflates and application to novel synthesis of indoles. Tetrahedron Lett. 2001, 42, 5275-5278.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 5275-5278
    • Dai, W.-M.1    Guo, D.-S.2    Sun, L.-P.3
  • 18
    • 0032514972 scopus 로고    scopus 로고
    • Improved procedures for the palladium-catalyzed coupling of terminal alkynes with aryl bromides (Sonogashira coupling)
    • (a) Thorand, S.; Krause, N. Improved procedures for the palladium-catalyzed coupling of terminal alkynes with aryl bromides (Sonogashira coupling). J. Org. Chem. 1998, 63, 8551-8553;
    • (1998) J. Org. Chem. , vol.63 , pp. 8551-8553
    • Thorand, S.1    Krause, N.2
  • 19
    • 0027378315 scopus 로고
    • An efficient palladium-catalysed reaction of vinyl and aryl halides or triflates with terminal alkynes
    • (b) Alami, M.; Ferri, F.; Linstrumelle, G. An efficient palladium-catalysed reaction of vinyl and aryl halides or triflates with terminal alkynes. Tetrahedron Lett. 1993, 34, 6403-6406;
    • (1993) Tetrahedron Lett. , vol.34 , pp. 6403-6406
    • Alami, M.1    Ferri, F.2    Linstrumelle, G.3
  • 20
    • 0000459210 scopus 로고    scopus 로고
    • 2 in piperidine: Versatile catalysts for Sonogashira reaction of vinyl chlorides at room temperature
    • 2 in piperidine: Versatile catalysts for Sonogashira reaction of vinyl chlorides at room temperature. J. Organomet. Chem. 2001, 624, 114-123.
    • (2001) J. Organomet. Chem. , vol.624 , pp. 114-123
    • Alami, M.1    Crousse, B.2    Ferri, F.3
  • 21
    • 35748932693 scopus 로고    scopus 로고
    • Supported copper precatalysts for ligand-free, palladium-free Sonogashira coupling reactions
    • Biffis, A.; Scattolin, E.; Ravasio, N.; Zaccheria, F. Supported copper precatalysts for ligand-free, palladium-free Sonogashira coupling reactions. Tetrahedron Lett. 2007, 48, 8761-8764.
    • (2007) Tetrahedron Lett. , vol.48 , pp. 8761-8764
    • Biffis, A.1    Scattolin, E.2    Ravasio, N.3    Zaccheria, F.4
  • 23
    • 0004252595 scopus 로고    scopus 로고
    • P. A. Grieco (Ed.); Blackie Academic & Professional: London
    • (b) Organic Synthesis in Water; P. A. Grieco (Ed.); Blackie Academic & Professional: London 1998;
    • (1998) Organic Synthesis in Water
  • 25
    • 0007512358 scopus 로고
    • Palladium-catalyzed alkylations in aqueous media
    • (a) Casalnuovo, A. L.; Calabrese, J. C. Palladium-catalyzed alkylations in aqueous media. J. Am. Chem. Soc. 1990, 112, 4324-4330;
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 4324-4330
    • Casalnuovo, A.L.1    Calabrese, J.C.2
  • 26
    • 8644224057 scopus 로고    scopus 로고
    • Palladium-catalyzed cross-coupling of aryl bromides under mild conditions, using water-soluble, sterically demanding alkylphosphines
    • (b) DeVasher, R. B.; Moore, L. R.; Shaughnessy, K. H. Aqueous-phase, palladium-catalyzed cross-coupling of aryl bromides under mild conditions, using water-soluble, sterically demanding alkylphosphines. J. Org. Chem. 2004, 69, 7919-7927;
    • (2004) J. Org. Chem. , vol.69 , pp. 7919-7927
    • Devasher, R.B.1    Moore, L.R.2    Aqueous-Phase, H.S.K.3
  • 27
    • 25844440760 scopus 로고    scopus 로고
    • General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water
    • (c) Anderson, K. W.; Buchwald, S. L. General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water. Angew. Chem. Int. Ed. 2005, 44, 6173-6177.
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 6173-6177
    • Anderson, K.W.1    Buchwald, S.L.2
  • 28
    • 0037136485 scopus 로고    scopus 로고
    • One-pot synthesis of symmetrical and unsymmetrical bisarylethynes by a modification of the Sonogashira coupling reaction
    • (d) Mio, M. J.; Kopel, L. C.; Braun, J. B.; Gadzikwa, T. L.; Hull, K. L.; Brisbois, R. G.; Markworth, C. J.; Grieco, P. A. One-pot synthesis of symmetrical and unsymmetrical bisarylethynes by a modification of the Sonogashira coupling reaction. Org. Lett. 2002, 4, 3199-3202;
    • (2002) Org. Lett. , vol.4 , pp. 3199-3202
    • Mio, M.J.1    Kopel, L.C.2    Braun, J.B.3    Gadzikwa, T.L.4    Hull, K.L.5    Brisbois, R.G.6    Markworth, C.J.7    Grieco, P.A.8
  • 30
    • 0012445118 scopus 로고    scopus 로고
    • Synthesis of N-(3-arylpropyl)amino acid derivatives by Sonogashira types of reaction in aqueous media
    • (f) Lo'pez-Deber, M. P.; Castedo, L.; Granja, J. R. Synthesis of N-(3-arylpropyl)amino acid derivatives by Sonogashira types of reaction in aqueous media. Org. Lett. 2001, 3, 2823-2826;
    • (2001) Org. Lett. , vol.3 , pp. 2823-2826
    • Lo'Pez-Deber, M.P.1    Castedo, L.2    Granja, J.R.3
  • 31
    • 0347992908 scopus 로고    scopus 로고
    • Transition-metal-free Sonogashira-type coupling reactions in water
    • (g) Appukkuttan, P.; Dehaen, W.; Van der Eycken, E. Transition-metal-free Sonogashira-type coupling reactions in water. Eur. J. Org. Chem. 2003, 68, 4713-4716.
    • (2003) Eur. J. Org. Chem. , vol.68 , pp. 4713-4716
    • Appukkuttan, P.1    Dehaen, W.2    Van Der Eycken, E.3
  • 33
    • 20844437157 scopus 로고
    • Diphenylthiirene 1-oxide: Synthesis, characterization, and reactivity
    • Carpino, L. A.; Chen, H. W. Diphenylthiirene 1-oxide: Synthesis, characterization, and reactivity. J. Am. Chem. Soc. 1979, 101, 390-394.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 390-394
    • Carpino, L.A.1    Chen, H.W.2
  • 34
    • 0035903909 scopus 로고    scopus 로고
    • Sonogashira coupling and cyclization reactions on alumina: A route to aryl alkynes, 2-substituted-benzo[b]-furans, and 2-substituted-indoles
    • Kabalka, G. W.; Wang, L.; Pagni, R. M. Sonogashira coupling and cyclization reactions on alumina: A route to aryl alkynes, 2-substituted- benzo[b]-furans, and 2-substituted-indoles. Tetrahedron 2001, 57, 8017-8028.
    • (2001) Tetrahedron , vol.57 , pp. 8017-8028
    • Kabalka, G.W.1    Wang, L.2    Pagni, R.M.3
  • 35
    • 34247276500 scopus 로고    scopus 로고
    • MCM-41-supported bidentate phosphine palladium(0) complex: a highly active and recyclable catalyst for the Sonogashira reaction of aryl iodides
    • DOI 10.1016/j.tet.2007.03.111, PII S0040402007005285
    • Cai, M.; Sha, J.; Xu, Q. MCM-41-supported bidentate phosphine palladium(0) complex: A highly active and recyclable catalyst for the Sonogashira reaction of aryl iodides. Tetrahedron 2007, 63, 4642-4647. (Pubitemid 46627811)
    • (2007) Tetrahedron , vol.63 , Issue.22 , pp. 4642-4647
    • Cai, M.1    Sha, J.2    Xu, Q.3
  • 36
    • 33645081197 scopus 로고    scopus 로고
    • A facile stereoselective synthesis of (2E)-3-silylallylic alcohols by hydromagnesiation of 1-aryl-2-silylacetylenes
    • Cai, M.; Zhou, Z.; Jiang, J. A facile stereoselective synthesis of (2E)-3-silylallylic alcohols by hydromagnesiation of 1-aryl-2-silylacetylenes. Eur. J. Org. Chem. 2006, 6, 1400-1402.
    • (2006) Eur. J. Org. Chem. , vol.6 , pp. 1400-1402
    • Cai, M.1    Zhou, Z.2    Jiang, J.3


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