메뉴 건너뛰기




Volumn 20, Issue 9, 2011, Pages 699-712

Synthesis and applications of poly(N-vinylimidazole) grafted silica-containing palladium nanoparticles as a new re-cyclable catalyst for Heck, Sonogashira and Suzuki coupling reactions

Author keywords

Heck reaction; Palladium nanoparticles; Poly(N vinylimidazole) grafted silica; Sonogashira reaction; Suzuki reaction

Indexed keywords

HECK REACTIONS; N-VINYLIMIDAZOLE; PALLADIUM NANOPARTICLES; SONOGASHIRA REACTIONS; SUZUKI REACTION;

EID: 80053355949     PISSN: 10261265     EISSN: 17355265     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (26)

References (48)
  • 3
    • 0036810670 scopus 로고    scopus 로고
    • Recoverable catalysts and reagents using recyclable polystyrene-based supports
    • DOI 10.1021/cr0103571
    • McNamara CA, Dixon MJ, Bradley M, Recoverable catalysts and reagents using recyclable polystyrene-based supports, Chem Rev, 102, 3275-3300, 2002. (Pubitemid 35350652)
    • (2002) Chemical Reviews , vol.102 , Issue.10 , pp. 3275-3300
    • McNamara, C.A.1    Dixon, M.J.2    Bradley, M.3
  • 4
    • 0035962701 scopus 로고    scopus 로고
    • Polymer-supported catalysis in synthetic organic chemistry
    • DOI 10.1016/S0040-4020(01)00298-8, PII S0040402001002988
    • Clapham B, Reger TS, Janda KD, Polymersupported catalysis in synthetic organic chemistry, Tetrahedron, 57, 4637-4662, 2001. (Pubitemid 32497204)
    • (2001) Tetrahedron , vol.57 , Issue.22 , pp. 4637-4662
    • Clapham, B.1    Reger, T.S.2    Janda, K.D.3
  • 5
    • 65349139123 scopus 로고    scopus 로고
    • Organic polymer supports for synthesis and for reagent and catalyst immobilization
    • Lu J, Toy PH, Organic polymer supports for synthesis and for reagent and catalyst immobilization, Chem Rev, 109, 815-838, 2009.
    • (2009) Chem Rev , vol.109 , pp. 815-838
    • Lu, J.1    Toy, P.H.2
  • 8
    • 33750699311 scopus 로고    scopus 로고
    • Preparation and properties of biocompatible polymer-grafted silica nanoparticle
    • DOI 10.1016/j.eurpolymj.2006.08.015, PII S0014305706002801
    • Yokoyama R, Suzuki S, Shirai K, Yamauchi T, Tsubokawa N, Tsuchimochi M, Preparation and properties of biocompatible polymer-grafted silica nanoparticle, Eur Polym J, 42, 3221-3229, 2006. (Pubitemid 44708910)
    • (2006) European Polymer Journal , vol.42 , Issue.12 , pp. 3221-3229
    • Yokoyama, R.1    Suzuki, S.2    Shirai, K.3    Yamauchi, T.4    Tsubokawa, N.5    Tsuchimochi, M.6
  • 9
    • 14844349822 scopus 로고    scopus 로고
    • 'Graft from' polymerization on colloidal silica particles: Elaboration of alkoxyamine grafted surface by in situ trapping of carbon radicals
    • DOI 10.1016/j.polymer.2005.01.032
    • Inoubli R, Dagreou S, Khoukh A, Roby F, Peyrelasse J, Billon L, Graft from polymerization on colloidal silica particles: elaboration of alkoxyamine grafted surface by in situ trapping of carbon radicals, Polymer, 46, 2486-2496, 2005. (Pubitemid 40353677)
    • (2005) Polymer , vol.46 , Issue.8 , pp. 2486-2496
    • Inoubli, R.1    Dagreou, S.2    Khoukh, A.3    Roby, F.4    Peyrelasse, J.5    Billon, L.6
  • 10
    • 0026821460 scopus 로고
    • Permeability of graft-polymerized polyvinyl-pyrrolidone-silica resin in packed columns
    • Cohen Y, Eisenberg P, Chaimberg M, Permeability of graft-polymerized polyvinyl-pyrrolidone-silica resin in packed columns, J Coll Inter Sci, 148, 579-586, 1992.
    • (1992) J Coll Inter Sci , vol.148 , pp. 579-586
    • Cohen, Y.1    Eisenberg, P.2    Chaimberg, M.3
  • 12
    • 1642418861 scopus 로고    scopus 로고
    • Polymer brushes via surface-initiated polymerizations
    • Edmondson S, Osborne VL, Huck WTS, Polymer brushes via surface-initiated polymerizations (Review), Chem Soc Rev, 33, 14-22, 2004. (Pubitemid 38376607)
    • (2004) Chemical Society Reviews , vol.33 , Issue.1 , pp. 14-22
    • Edmondson, S.1    Osborne, V.L.2    Huck, W.T.S.3
  • 13
    • 73249145595 scopus 로고    scopus 로고
    • Polymer brushes via surface-initiated controlled radical polymerization: Synthesis, characterization, properties, and applications
    • Barbey R, Lavanant L, Paripovic D, Schuwer N, Sugnaux C, Tugulu S, Klok H-A, Polymer brushes via surface-initiated controlled radical polymerization: synthesis, characterization, properties, and applications, Chem Rev, 109, 5437-5527, 2009.
    • (2009) Chem Rev , vol.109 , pp. 5437-5527
    • Barbey, R.1    Lavanant, L.2    Paripovic, D.3    Schuwer, N.4    Sugnaux, C.5    Tugulu, S.6    Klok, H.-A.7
  • 14
    • 33947328224 scopus 로고    scopus 로고
    • Graft polymerization of styrene initiated by covalently bonded peroxide groups on silica
    • DOI 10.1016/j.jcis.2007.02.002, PII S0021979707001671
    • Bachmann S, Wang H, Albert K, Partch R, Graft polymerization of styrene initiated by covalently bonded peroxide groups on silica, J Coll Inter Sci, 309, 169-175, 2007. (Pubitemid 46440970)
    • (2007) Journal of Colloid and Interface Science , vol.309 , Issue.1 , pp. 169-175
    • Bachmann, S.1    Wang, H.2    Albert, K.3    Partch, R.4
  • 15
    • 0037427643 scopus 로고    scopus 로고
    • Graft polymerization of vinyl acetate onto silica
    • Nguyen V, Yoshida W, Cohen Y, Graft polymerization of vinyl acetate onto silica, J Appl Polym Sci, 87, 300-310, 2003.
    • (2003) J Appl Polym Sci , vol.87 , pp. 300-310
    • Nguyen, V.1    Yoshida, W.2    Cohen, Y.3
  • 16
    • 39849102965 scopus 로고    scopus 로고
    • A novel hydrophilic polymer-ceramic composite membrane 1: Acrylic acid grafting membrane
    • Cao X, Zhang T, Nguyen QT, Zhang Y, Ping Z, A novel hydrophilic polymer-ceramic composite membrane 1: acrylic acid grafting membrane, J Membr Sci, 312, 15-22, 2008.
    • (2008) J Membr Sci , vol.312 , pp. 15-22
    • Cao, X.1    Zhang, T.2    Nguyen, Q.T.3    Zhang, Y.4    Ping, Z.5
  • 17
    • 34547207599 scopus 로고    scopus 로고
    • Synthesis of poly(methyl acrylate) crafted onto silica particles by Z-supported RAFT polymerization
    • DOI 10.1002/masy.200750210
    • Zhao Y, Perrier S, Synthesis of poly (methyl acrylate) grafted onto silica particles by Z-supported RAFT polymerization, Macromol Symp, 248, 94-103, 2007. (Pubitemid 47119100)
    • (2007) Macromolecular Symposia , vol.248 , pp. 94-103
    • Zhao, Y.1    Perrier, S.2
  • 18
    • 0025230788 scopus 로고
    • Reversed phase and normal phase liquid chromatography on poly(1-vinyl-2-pyrrolidone) or poly(1-vinylimidazole) bonded silica using methacryloxypropyltrimethoxysilane as coupling agent. Stationary phases 23
    • Kou CR, Enoh HD, Huang CC, Den TG, Reversed phase and normal phase liquid chromatography on poly (1-vinyl-2-pyrrolidone) or poly (1-vinylimidazole) bonded silica using y-methacryloxypropyltrimethoxysilane as coupling agent stationary phases, Fresenius J Anal Chem, 336, 409-414, 1990. (Pubitemid 20147142)
    • (1990) Fresenius' Journal of Analytical Chemistry , vol.336 , Issue.5 , pp. 409-414
    • Kou, C.R.1    Luoh, H.D.2    Huang, C.C.3    Den, T.G.4
  • 19
    • 43049161286 scopus 로고    scopus 로고
    • Preparation and catalytic activity of P4VP-Cu (II) complex supported on silica gel
    • Gao B, Kong D, Zhang Y, Preparation and catalytic activity of P4VP-Cu (II) complex supported on silica gel, J Mol Catal A: Chem, 286, 143-148, 2008.
    • (2008) J Mol Catal A: Chem , vol.286 , pp. 143-148
    • Gao, B.1    Kong, D.2    Zhang, Y.3
  • 24
    • 33846893890 scopus 로고    scopus 로고
    • Carbon-carbon coupling reactions catalyzed by heterogeneous palladium catalysts
    • DOI 10.1021/cr0505674
    • Yin L, Liebscher J, Carbon-carbon coupling reactions catalyzed by heterogeneous palladium catalysts, Chem Rev, 107, 133-173, 2007. (Pubitemid 46223705)
    • (2007) Chemical Reviews , vol.107 , Issue.1 , pp. 133-173
    • Yin, L.1    Liebscher, J.2
  • 25
    • 33645896595 scopus 로고
    • Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides
    • Heck RF, Nolley JP, Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides, J Org Chem, 37, 2320-2322, 1972.
    • (1972) J Org Chem , vol.37 , pp. 2320-2322
    • Heck, R.F.1    Nolley, J.P.2
  • 26
    • 0034249671 scopus 로고    scopus 로고
    • The Heck reaction as a sharpening stone of palladium catalysis
    • Beletskaya IP, Cheprakov AV, The Heck reaction as a sharpening stone of palladium catalysis, Chem Rev, 100, 3009-3066, 2000.
    • (2000) Chem Rev , vol.100 , pp. 3009-3066
    • Beletskaya, I.P.1    Cheprakov, A.V.2
  • 27
    • 34250157778 scopus 로고    scopus 로고
    • Silica-supported Pd catalysts for Heck coupling reactions
    • DOI 10.1016/j.tet.2007.04.023, PII S0040402007006424
    • Polshettiwar V, Molnar A, Silica-supported Pd catalysts for Heck coupling reactions, Tetrahedron, 63, 6949-6976, 2007. (Pubitemid 46894725)
    • (2007) Tetrahedron , vol.63 , Issue.30 , pp. 6949-6976
    • Polshettiwar, V.1    Molnar, A.2
  • 28
    • 0037943974 scopus 로고    scopus 로고
    • Palladium-catalyzed alkynylation
    • Negishi E, Anastasia L, Palladium-catalyzed alkynylation, Chem Rev, 103, 1979-2017, 2003.
    • (2003) Chem Rev , vol.103 , pp. 1979-2017
    • Negishi, E.1    Anastasia, L.2
  • 30
    • 33947727055 scopus 로고    scopus 로고
    • The Sonogashira reaction: A booming methodology in synthetic organic chemistry
    • DOI 10.1021/cr050992x
    • Chinchilla R, Najera C, The Sonogashira reaction: a booming methodology in synthetic organic chemistry, Chem Rev, 107, 874-922, 2007. (Pubitemid 46504819)
    • (2007) Chemical Reviews , vol.107 , Issue.3 , pp. 874-922
    • Chinchilla, R.1    Najera, C.2
  • 31
    • 2042507954 scopus 로고
    • Palladium-catalyzed cross coupling reactions of organoboron compounds
    • Miyaura N, Suzuki A, Palladium-catalyzed cross coupling reactions of organoboron compounds, Chem Rev, 95, 2457-2483, 1995.
    • (1995) Chem Rev , vol.95 , pp. 2457-2483
    • Miyaura, N.1    Suzuki, A.2
  • 32
    • 39749179066 scopus 로고    scopus 로고
    • Non-conventional methodologies for transition-metal catalyzed carbon-carbon coupling: A critical overview. Part 2: The Suzuki reaction
    • Alonso F, Beletskaya IP, Yus M, Non-conventional methodologies for transition-metal catalyzed carbon-carbon coupling: a critical overview. Part 2: The Suzuki reaction, Tetrahedron, 64, 3047-3101, 2008.
    • (2008) Tetrahedron , vol.64 , pp. 3047-3101
    • Alonso, F.1    Beletskaya, I.P.2    Yus, M.3
  • 33
    • 34548042264 scopus 로고    scopus 로고
    • Palladium supported on poly(N-vinylimidazole) or poly(N-vinylimidazole- co-N-vinylcaprolactam) as a new recyclable catalyst for the Mizoroki-Heck reaction
    • DOI 10.1016/j.jorganchem.2007.06.056, PII S0022328X07004743
    • Beletskaya IP, Khokhlov AR, Tarasenko EA, Tyurin VS, Palladium supported on poly (N-vinylimidazole) or poly (N-vinylimidazole-co-N-vinylcaprolactam) as a new recyclable catalyst for the Mizoroki-Heck reaction, J Organomet Chem, 692, 4402-4406, 2007. (Pubitemid 47285176)
    • (2007) Journal of Organometallic Chemistry , vol.692 , Issue.20 , pp. 4402-4406
    • Beletskaya, I.P.1    Khokhlov, A.R.2    Tarasenko, E.A.3    Tyurin, V.S.4
  • 34
    • 0141738306 scopus 로고    scopus 로고
    • Silica-supported 3-4, 5-dihydroimidazol-1- ylpropyltriethoxysilanedichloropalladium (II) complex: Heck and Suzuki cross-coupling reactions
    • Gurbuz N, Ozdemir I, Cetinkaya B, Seckin T, Silica-supported 3-4, 5-dihydroimidazol-1-ylpropyltriethoxysilanedichloropalladium (II) complex: Heck and Suzuki cross-coupling reactions, Appl Organomet Chem, 17, 776-780, 2003.
    • (2003) Appl Organomet Chem , vol.17 , pp. 776-780
    • Gurbuz, N.1    Ozdemir, I.2    Cetinkaya, B.3    Seckin, T.4
  • 35
    • 34748877638 scopus 로고    scopus 로고
    • Pd nanoparticles embedded in sponge-like porous silica as a Suzuki-Miyaura catalyst: Similarities and differences with homogeneous catalysts
    • DOI 10.1016/j.jcat.2007.07.027, PII S0021951707003132
    • Budroni G, Corma A, Garcia H, Primo A, Pd nanoparticles embedded in sponge-like porous silica as a Suzuki-Miyaura catalyst: similarities and differences with homogeneous catalysts, J Catal, 251, 345-353, 2007. (Pubitemid 47488311)
    • (2007) Journal of Catalysis , vol.251 , Issue.2 , pp. 345-353
    • Budroni, G.1    Corma, A.2    Garcia, H.3    Primo, A.4
  • 36
    • 13444269340 scopus 로고    scopus 로고
    • A periodic mesoporous organosilica containing a carbapalladacycle complex as heterogeneous catalyst for Suzuki cross-coupling
    • DOI 10.1016/j.jcat.2004.11.006, PII S0021951704005329
    • Corma A, Das D, Garcia H, Leyva A, A periodic mesoporous organosilica containing a carbapalladacycle complex as heterogeneous catalyst for Suzuki cross-coupling, J Catal, 229, 322-331, 2005. (Pubitemid 40215176)
    • (2005) Journal of Catalysis , vol.229 , Issue.2 , pp. 322-331
    • Corma, A.1    Das, D.2    Garcia, H.3    Leyva, A.4
  • 37
    • 77955514162 scopus 로고    scopus 로고
    • Palladium catalysts deposited on silica materials: Comparison of catalysts based on mesoporous and amorphous supports in Heck reaction
    • Demel J, Cejka J, Stepnicka P, Palladium catalysts deposited on silica materials: comparison of catalysts based on mesoporous and amorphous supports in Heck reaction, J Mol Catal A: Chem, 329, 13-20, 2010.
    • (2010) J Mol Catal A: Chem , vol.329 , pp. 13-20
    • Demel, J.1    Cejka, J.2    Stepnicka, P.3
  • 38
    • 79956188204 scopus 로고    scopus 로고
    • Reductive dehalogenation of aryl halides over palladium catalysts deposited on SBA-15 type molecular sieve modified with amine donor groups
    • Stepnicka P, Semler M, Demel J, Zukal A, Cejka J, Reductive dehalogenation of aryl halides over palladium catalysts deposited on SBA-15 type molecular sieve modified with amine donor groups, J Mol Catal A: Chem, 341, 97-102, 2011.
    • (2011) J Mol Catal A: Chem , vol.341 , pp. 97-102
    • Stepnicka, P.1    Semler, M.2    Demel, J.3    Zukal, A.4    Cejka, J.5
  • 39
    • 62649107110 scopus 로고    scopus 로고
    • Preparation of heterogeneous catalysts supported on mesoporous molecular sieves modified with various N-groups and their use in the Heck reaction
    • Demel J, Sujandi, Park S-E, Cejka J, Stepnicka P, Preparation of heterogeneous catalysts supported on mesoporous molecular sieves modified with various N-groups and their use in the Heck reaction, J Mol Catal A: Chem, 302, 28-35, 2009.
    • (2009) J Mol Catal A: Chem , vol.302 , pp. 28-35
    • Demel, J.1    Sujandi, P.S.-E.2    Cejka, J.3    Stepnicka, P.4
  • 40
    • 77950296598 scopus 로고    scopus 로고
    • Palladium nanoparticles supported on modified crosslinked polyacrylamide containing phosphinite ligand: A novel and efficient heterogeneous catalyst for carbon-carbon cross-coupling reactions
    • Tamami B, Ghasemi S, Palladium nanoparticles supported on modified crosslinked polyacrylamide containing phosphinite ligand: a novel and efficient heterogeneous catalyst for carbon-carbon cross-coupling reactions, J Mol Catal A: Chem, 322, 98-105, 2010.
    • (2010) J Mol Catal A: Chem , vol.322 , pp. 98-105
    • Tamami, B.1    Ghasemi, S.2
  • 41
    • 79251498332 scopus 로고    scopus 로고
    • Synthesis and applications of polyvinylpyridine-grafted silica containing palladium nanoparticles as a new heterogeneous catalyst for Heck and Suzuki coupling reactions
    • Tamami B, Farjadian F, Synthesis and applications of polyvinylpyridine- grafted silica containing palladium nanoparticles as a new heterogeneous catalyst for Heck and Suzuki coupling reactions, J Iran Chem Soc, 8, S77-S88, 2011.
    • (2011) J Iran Chem Soc , vol.8
    • Tamami, B.1    Farjadian, F.2
  • 42
    • 78651258995 scopus 로고    scopus 로고
    • Palladium nanoparticles supported on poly (N-vinylpyrrolidone)-grafted silica as new recyclable catalyst for Heck cross-coupling reactions
    • Tamami B, Allahyari H, Ghasemi S, Farjadian F, Palladium nanoparticles supported on poly (N-vinylpyrrolidone)-grafted silica as new recyclable catalyst for Heck cross-coupling reactions, J Organomet Chem, 696, 594-599, 2011.
    • (2011) J Organomet Chem , vol.696 , pp. 594-599
    • Tamami, B.1    Allahyari, H.2    Ghasemi, S.3    Farjadian, F.4
  • 43
    • 25444441550 scopus 로고    scopus 로고
    • Investigation of Pd leaching from supported Pd catalysts during the Heck reaction
    • Ji Y, Jain S, Davis RJ, Investigation of Pd leaching from supported Pd catalysts during the Heck reaction, J Phys Chem, 109, 17232-17238, 2005.
    • (2005) J Phys Chem , vol.109 , pp. 17232-17238
    • Ji, Y.1    Jain, S.2    Davis, R.J.3
  • 44
    • 33846922255 scopus 로고    scopus 로고
    • Palladium (0) complexes of (P, P) and (P, N) ligands immobilized on silica gel as catalysts in selective Heck type carbon-carbon coupling reactions
    • Singh G, Bali S, Singh AK, Palladium (0) complexes of (P, P) and (P, N) ligands immobilized on silica gel as catalysts in selective Heck type carbon-carbon coupling reactions, Polyhedron, 26, 897-903, 2007.
    • (2007) Polyhedron , vol.26 , pp. 897-903
    • Singh, G.1    Bali, S.2    Singh, A.K.3
  • 45
    • 0043198693 scopus 로고    scopus 로고
    • Silica-supported polymeric palladium (0) complexes as catalysts for Heck reaction in organic synthesis
    • Zhao S-F, Zhou R-X, Yang Y-F, Zheng X-M, Silica-supported polymeric palladium (0) complexes as catalysts for Heck reaction in organic synthesis, React Kinet Catal Lett, 79, 333-340, 2003.
    • (2003) React Kinet Catal Lett , vol.79 , pp. 333-340
    • Zhao, S.-F.1    Zhou, R.-X.2    Yang, Y.-F.3    Zheng, X.-M.4
  • 46
    • 33745698740 scopus 로고    scopus 로고
    • Highly dispersed nickel and palladium nanoparticle silica aerogels: Sol-gel processing of tethered metal complexes and application as catalysts in the Mizoroki-Heck reaction
    • DOI 10.1039/b604544h
    • Martinez S, Moreno-Man M, Vallribera A, Schubert U, Roig A, Molins E, Highly dispersed nickel and palladium nanoparticle silica aerogels: sol-gel processing of tethered metal complexes and application as catalysts in the Mizoroki-Heck reaction, New J Chem, 30, 1093-1097, 2006. (Pubitemid 44000945)
    • (2006) New Journal of Chemistry , vol.30 , Issue.7 , pp. 1093-1097
    • Martinez, S.1    Moreno-Manas, M.2    Vallribera, A.3    Schubert, U.4    Roig, A.5    Molins, E.6
  • 47
    • 55749085477 scopus 로고    scopus 로고
    • Palladium immobilized on silica gel: A novel and reusable catalyst for Heck reaction
    • Wang Z-L, Wang L, Yan J-C, Palladium immobilized on silica gel: a novel and reusable catalyst for Heck reaction, Chin J Chem, 26, 1721-1726, 2008.
    • (2008) Chin J Chem , vol.26 , pp. 1721-1726
    • Wang, Z.-L.1    Wang, L.2    Yan, J.-C.3
  • 48
    • 0037834588 scopus 로고    scopus 로고
    • The first synthesis of stable palladium (II) PCP-type catalysts supported on silica-application to the Heck reaction
    • Chanthateyanonth R, Alper H, The first synthesis of stable palladium (II) PCP-type catalysts supported on silica-application to the Heck reaction, J Mol Catal A: Chem, 201, 23-31, 2003.
    • (2003) J Mol Catal A: Chem , vol.201 , pp. 23-31
    • Chanthateyanonth, R.1    Alper, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.