메뉴 건너뛰기




Volumn 38, Issue 14, 2008, Pages 2285-2298

Immobilization of Pd catalysts on mesoporous silica for amine- and copper-free Sonogashira coupling reactions

Author keywords

Mesoporous silica; Pd catalyst immobilization; Sonogashira coupling

Indexed keywords

3 AMINOPROPYLTRIETHOXYSILANE; ALKYNE DERIVATIVE; AMINE; COPPER; DIPHENYLPHOSPHINE; PALLADIUM; PHOSPHINE DERIVATIVE; SILICON DIOXIDE;

EID: 47249116970     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802138546     Document Type: Article
Times cited : (12)

References (30)
  • 1
    • 9644285669 scopus 로고
    • Convenient synthesis of acetylenes: Catalytic substitutions of acetylenic hydrogen with bromo alkenes, iodoarenes, and bromopyridines
    • Sonogashira, K.; Tohda, Y.; Hagihara, N. Convenient synthesis of acetylenes: Catalytic substitutions of acetylenic hydrogen with bromo alkenes, 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
    • 0035874744 scopus 로고    scopus 로고
    • Rapid homogeneous-phase Sonogashira coupling reactions using controlled microwave heating
    • Erdelyi, M.; Gogoll, A. Rapid homogeneous-phase Sonogashira coupling reactions using controlled microwave heating. J. Org. Chem. 2001, 66, 4165-4169.
    • (2001) J. Org. Chem , vol.66 , pp. 4165-4169
    • Erdelyi, M.1    Gogoll, A.2
  • 3
    • 0032046415 scopus 로고    scopus 로고
    • Synthesis of α,ω- difunctionalized oligo- and poly(p-phenyleneethynylene)s
    • Francke, V.; Mangel, T.; Muullen, K. Synthesis of α,ω- difunctionalized oligo- and poly(p-phenyleneethynylene)s. Macromolecules 1998, 31, 2447-2453.
    • (1998) Macromolecules , vol.31 , pp. 2447-2453
    • Francke, V.1    Mangel, T.2    Muullen, K.3
  • 4
    • 0028312651 scopus 로고
    • Rigid rod conjugated polymers for nonlinear optics, 1: Characterization and linear optical properties of poly-(aryleneethynylene) derivatives
    • Moroni, M.; Lemoigne, J.; Luzzati, S. Rigid rod conjugated polymers for nonlinear optics, 1: Characterization and linear optical properties of poly-(aryleneethynylene) derivatives. Macromolecules 1994, 27, 562-571.
    • (1994) Macromolecules , vol.27 , pp. 562-571
    • Moroni, M.1    Lemoigne, J.2    Luzzati, S.3
  • 5
    • 33749111932 scopus 로고
    • Iterative divergent/convergent approach to linear conjugated oligomers by successive doubling of the molecular length: A rapid route to a 128-Å-long potential molecular wire
    • Schumm, J. S.; Pearson, D. L.; Tour, J. M. Iterative divergent/convergent approach to linear conjugated oligomers by successive doubling of the molecular length: A rapid route to a 128-Å-long potential molecular wire. Angew. Chem., Int. Ed. Engl. 1994, 33, 1360-1363.
    • (1994) Angew. Chem., Int. Ed. Engl , vol.33 , pp. 1360-1363
    • Schumm, J.S.1    Pearson, D.L.2    Tour, J.M.3
  • 7
    • 0034604562 scopus 로고    scopus 로고
    • Acetylenic coupling: A powerful tool in molecular construction
    • Siemsen, P.; Livingston, R. C.; Diederich, F. Acetylenic coupling: A powerful tool in molecular construction. Angew. Chem. Int. Ed. Engl. 2000, 39, 2632-2657.
    • (2000) Angew. Chem. Int. Ed. Engl , vol.39 , pp. 2632-2657
    • Siemsen, P.1    Livingston, R.C.2    Diederich, F.3
  • 8
    • 4043066278 scopus 로고    scopus 로고
    • Ligand- copper-, and amine-free Sonogashira reaction of aryl iodides and bromides with terminal alkynes
    • Urgaonkar, S.; Verkade, J. G. Ligand- copper-, and amine-free Sonogashira reaction of aryl iodides and bromides with terminal alkynes. J. Org. Chem. 2004, 69, 5752-5755.
    • (2004) J. Org. Chem , vol.69 , pp. 5752-5755
    • Urgaonkar, S.1    Verkade, J.G.2
  • 9
    • 23444461726 scopus 로고    scopus 로고
    • Application of recoverable nanosized palladium(0) catalyst in Sonogashira reaction
    • Li, P.; Wang, L.; Li, H. Application of recoverable nanosized palladium(0) catalyst in Sonogashira reaction. Tetrahedron 2005, 61, 8633-8640.
    • (2005) Tetrahedron , vol.61 , pp. 8633-8640
    • Li, P.1    Wang, L.2    Li, H.3
  • 10
    • 0033526360 scopus 로고    scopus 로고
    • Polymer-supported chiral Co(salen) complexes: Synthetic applications and mechanistic investigations in the hydrolytic kinetic resolution of terminal epoxides
    • Annis, D. A.; Jacobsen, E. N. Polymer-supported chiral Co(salen) complexes: Synthetic applications and mechanistic investigations in the hydrolytic kinetic resolution of terminal epoxides. J. Am. Chem. Soc. 1999, 121, 4147-4154.
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 4147-4154
    • Annis, D.A.1    Jacobsen, E.N.2
  • 11
    • 0034624412 scopus 로고    scopus 로고
    • Hydroformylation reactions using recyclable rhodium-complexed dendrimers on silica
    • Bourque, S. C.; Alper, H. Hydroformylation reactions using recyclable rhodium-complexed dendrimers on silica. J. Am. Chem. Soc. 2000, 122, 956-957.
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 956-957
    • Bourque, S.C.1    Alper, H.2
  • 12
    • 0033407595 scopus 로고    scopus 로고
    • Enantioselective allylic alkylation using polymer-supported palladium catalysts
    • (a) Hallmann, K.; Macedo, E.; Nordstrom, K.; Moberg, C. Enantioselective allylic alkylation using polymer-supported palladium catalysts. Tetrahedron: Asymmetry 1999, 10, 4037-4046;
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 4037-4046
    • Hallmann, K.1    Macedo, E.2    Nordstrom, K.3    Moberg, C.4
  • 13
    • 0033529906 scopus 로고    scopus 로고
    • An easily prepared, air and moisture stable, resin-bound palladium catalyst for Suzuki cross-coupling reactions
    • (b) Zhang, T. Y., Allen, M. J. An easily prepared, air and moisture stable, resin-bound palladium catalyst for Suzuki cross-coupling reactions. Tetrahedron Lett. 1999, 40, 5813-5816.
    • (1999) Tetrahedron Lett , vol.40 , pp. 5813-5816
    • Zhang, T.Y.1    Allen, M.J.2
  • 14
    • 0141852891 scopus 로고    scopus 로고
    • Polystyrene-supported recyclable palladacycle catalyst for Heck, Suzuki and Sonogashira reactions
    • Lin, C.-A.; Luo, F.-T. Polystyrene-supported recyclable palladacycle catalyst for Heck, Suzuki and Sonogashira reactions. Tetrahedron Lett. 2003, 44, 7565-7568.
    • (2003) Tetrahedron Lett , vol.44 , pp. 7565-7568
    • Lin, C.-A.1    Luo, F.-T.2
  • 15
    • 1642578978 scopus 로고    scopus 로고
    • Sonogashira cross-coupling reactions catalysed by heterogeneous copper-free Pd-zeolites
    • Djakovitch, L.; Rollet, P. Sonogashira cross-coupling reactions catalysed by heterogeneous copper-free Pd-zeolites. Tetrahedron Lett. 2004, 45, 1367-1370.
    • (2004) Tetrahedron Lett , vol.45 , pp. 1367-1370
    • Djakovitch, L.1    Rollet, P.2
  • 16
    • 0037561597 scopus 로고    scopus 로고
    • An easily accessible resin-supported palladium catalyst for Sonogashira coupling
    • Gonthier, E.; Breinbauer, R. An easily accessible resin-supported palladium catalyst for Sonogashira coupling. Synlett 2003, 1049-1051.
    • (2003) Synlett , pp. 1049-1051
    • Gonthier, E.1    Breinbauer, R.2
  • 17
    • 14644439171 scopus 로고    scopus 로고
    • A novel silica-supported palladium catalyst for a copper-free Sonogashira coupling reaction
    • Tyrrell, E.; Al-Saardi, A.; Miller, J. A novel silica-supported palladium catalyst for a copper-free Sonogashira coupling reaction. Synlett 2005, 487-488.
    • (2005) Synlett , pp. 487-488
    • Tyrrell, E.1    Al-Saardi, A.2    Miller, J.3
  • 18
    • 0026931265 scopus 로고
    • Ordered mesoporous molecular sieves synthesized by a liquid-crystal template mechanism
    • Kresge, C. T.; Leonowicz, M. E.; Roth, W. J.; Vartuli, J. C.; Beck, J. S. Ordered mesoporous molecular sieves synthesized by a liquid-crystal template mechanism. Nature 1992, 359, 710-712.
    • (1992) Nature , vol.359 , pp. 710-712
    • Kresge, C.T.1    Leonowicz, M.E.2    Roth, W.J.3    Vartuli, J.C.4    Beck, J.S.5
  • 19
    • 0034839549 scopus 로고    scopus 로고
    • Imprinted polysilsesquioxanes for the enhanced recognition of metal ions
    • Burleigh, M. C.; Dai, S.; Hagaman, E. W.; Lin, J. S. Imprinted polysilsesquioxanes for the enhanced recognition of metal ions. Chem. Mater. 2001, 13, 2537-2546.
    • (2001) Chem. Mater , vol.13 , pp. 2537-2546
    • Burleigh, M.C.1    Dai, S.2    Hagaman, E.W.3    Lin, J.S.4
  • 20
    • 0032559316 scopus 로고    scopus 로고
    • Triblock copolymer syntheses of mesoporous silica with periodic 50 to 300 angstrom pores
    • Zhao, D.; Feng, J.; Huo, Q.; Melosh, N.; Fredrickson, G. H.; Chmelka, B.; Stucky, G. D. Triblock copolymer syntheses of mesoporous silica with periodic 50 to 300 angstrom pores. Science 1998, 279, 548-552.
    • (1998) Science , vol.279 , pp. 548-552
    • Zhao, D.1    Feng, J.2    Huo, Q.3    Melosh, N.4    Fredrickson, G.H.5    Chmelka, B.6    Stucky, G.D.7
  • 24
    • 22244461931 scopus 로고    scopus 로고
    • Mercaptopropyl-modified mesoporous silica: A remarkable support for the preparation of a reusable, heterogeneous palladium catalyst for coupling reactions
    • Crudden, C. M.; Sateesh, M.; Lewis, R. Mercaptopropyl-modified mesoporous silica: A remarkable support for the preparation of a reusable, heterogeneous palladium catalyst for coupling reactions. J. Am. Chem. Soc. 2005, 127, 10045-10050.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 10045-10050
    • Crudden, C.M.1    Sateesh, M.2    Lewis, R.3
  • 26
    • 0034670644 scopus 로고    scopus 로고
    • Reaction of (3-aminopropyl) dimethylethoxysilane with amine catalysts on silica surfaces
    • White, L. D.; Tripp, C. P. Reaction of (3-aminopropyl) dimethylethoxysilane with amine catalysts on silica surfaces. J. Colloid Interface Sci. 2000, 232, 400-407.
    • (2000) J. Colloid Interface Sci , vol.232 , pp. 400-407
    • White, L.D.1    Tripp, C.P.2
  • 28
    • 0345356279 scopus 로고    scopus 로고
    • Functionalization of SBA-15 with APTES and characterization of functionalized materials
    • Chong, A. S. M.; Zhao, X. S. Functionalization of SBA-15 with APTES and characterization of functionalized materials. J. Phys. Chem. B 2003, 107, 12650-12657.
    • (2003) J. Phys. Chem. B , vol.107 , pp. 12650-12657
    • Chong, A.S.M.1    Zhao, X.S.2
  • 29
    • 20344391381 scopus 로고    scopus 로고
    • Copper- and ligand-free Sonogashira reaction catalyzed by Pd(0) nanoparticles at ambient conditions under ultrasound irradiation
    • Gholap, A. R.; Venkatesan, K.; Pasricha, R.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. Copper- and ligand-free Sonogashira reaction catalyzed by Pd(0) nanoparticles at ambient conditions under ultrasound irradiation. J. Org. Chem. 2005, 70, 4869-4872.
    • (2005) J. Org. Chem , vol.70 , pp. 4869-4872
    • Gholap, A.R.1    Venkatesan, K.2    Pasricha, R.3    Daniel, T.4    Lahoti, R.J.5    Srinivasan, K.V.6
  • 30
    • 0041364065 scopus 로고    scopus 로고
    • Sonogashira coupling reaction with diminished homocoupling
    • Elangovan, A.; Wang, Y.; Ho, T. Sonogashira coupling reaction with diminished homocoupling. Org. Lett. 2003, 5, 1841-1844.
    • (2003) Org. Lett , vol.5 , pp. 1841-1844
    • Elangovan, A.1    Wang, Y.2    Ho, T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.