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Volumn 46, Issue 23, 2007, Pages 4329-4332

A magnetic-nanoparticle-supported 4-N,N-dialkylaminopyridine catalyst: Excellent reactivity combined with facile catalyst recovery and recyclability

Author keywords

4 N,N dialkylaminopyridines; Heterogeneous catalysis; Nanostructures; Nucleophilic reactions; Supported catalysts

Indexed keywords

4-N,N-DIALKYLAMINOPYRIDINES; NUCLEOPHILIC REACTIONS; SUPPORTED CATALYSTS;

EID: 34447285219     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200605216     Document Type: Article
Times cited : (250)

References (57)
  • 5
  • 26
    • 0036809927 scopus 로고    scopus 로고
    • General review: C. E. Song, S.-G. Lee, Chem. Rev. 2002, 102, 3495.
    • General review: C. E. Song, S.-G. Lee, Chem. Rev. 2002, 102, 3495.
  • 28
    • 34447287421 scopus 로고    scopus 로고
    • The authors reported a slow but appreciable rate of background acylation (33% yield compared to 93% for the catalyzed process) in the absence of catalyst under these conditions
    • The authors reported a slow but appreciable rate of background acylation (33% yield compared to 93% for the catalyzed process) in the absence of catalyst under these conditions.
  • 29
    • 34447278645 scopus 로고    scopus 로고
    • The catalyst is also an active promoter of the challenging Baylis-Hillman reaction at higher catalyst loadings 30 mol
    • The catalyst is also an active promoter of the challenging Baylis-Hillman reaction at higher catalyst loadings (30 mol%).
  • 31
    • 0037739323 scopus 로고    scopus 로고
    • For pioneering work on the development of highly active and recyclable homogeneous polymer-bound DMAP derivatives that can be precipitated/extracted after reaction, see: a D. E. Bergbreiter, P. L. Osburn, C. Li, Org. Lett. 2002, 4, 737;
    • For pioneering work on the development of highly active and recyclable homogeneous polymer-bound DMAP derivatives that can be precipitated/extracted after reaction, see: a) D. E. Bergbreiter, P. L. Osburn, C. Li, Org. Lett. 2002, 4, 737;
  • 35
  • 42
    • 33751108971 scopus 로고    scopus 로고
    • During the preparation of this manuscript, an achiral magnetic-nanoparticle-supported phase-transfer catalyst based on a quaternary ammonium salt was reported for the butylation of sodium phenoxide at 100°C. The catalyst is active at a loading of 4 mol% and could be recycled four times with only a 5% reduction in yield: M. Kawamura, K. Sato, Chem. Commun. 2006, 4718.
    • During the preparation of this manuscript, an achiral magnetic-nanoparticle-supported phase-transfer catalyst based on a quaternary ammonium salt was reported for the butylation of sodium phenoxide at 100°C. The catalyst is active at a loading of 4 mol% and could be recycled four times with only a 5% reduction in yield: M. Kawamura, K. Sato, Chem. Commun. 2006, 4718.
  • 43
    • 34447283122 scopus 로고    scopus 로고
    • Calculated from X-ray diffraction (XRD) data, using the Debye-Scherrer equation: R. M. Cornell, U. Schwertmann, The Iron Oxides, Wiley-VCH, Weinheim, 1996.
    • Calculated from X-ray diffraction (XRD) data, using the Debye-Scherrer equation: R. M. Cornell, U. Schwertmann, The Iron Oxides, Wiley-VCH, Weinheim, 1996.
  • 46
    • 34447275777 scopus 로고    scopus 로고
    • See the Supporting Information for details
    • See the Supporting Information for details.
  • 48
    • 34447269997 scopus 로고    scopus 로고
    • The nanoparticles were characterized by FTIR and Raman spectroscopy, XRD, and TEM. See the Supporting Information
    • The nanoparticles were characterized by FTIR and Raman spectroscopy, XRD, and TEM. See the Supporting Information.
  • 50
    • 33646542359 scopus 로고    scopus 로고
    • A particular cause for potential concern in the current study would be the ammonium-cation-binding properties of uncoated Fe3O4 nanoparticles; all reactions catalyzed by DMAP pass through key pyridinium-ion intermediates, while nucleophile-catalyzed acylations of alcohols in the presence of a stoichiometric amine base generate ammonium salts. For a recent report detailing the binding of magnetite to ammonium cations, see: W. Li, C. Gao, H. Qian, J. Ren, D. Yan, J. Mater. Chem. 2006, 16, 1852
    • 4 nanoparticles; all reactions catalyzed by DMAP pass through key pyridinium-ion intermediates, while nucleophile-catalyzed acylations of alcohols in the presence of a stoichiometric amine base generate ammonium salts. For a recent report detailing the binding of magnetite to ammonium cations, see: W. Li, C. Gao, H. Qian, J. Ren, D. Yan, J. Mater. Chem. 2006, 16, 1852.
  • 51
    • 34447283594 scopus 로고    scopus 로고
    • 1 can be prepared in one step from commercially available 4-N-methylpyridine (Aldrich) and (3-chloropropyl)triethoxysilane. See reference [7] or the Supporting Information for details.
    • 1 can be prepared in one step from commercially available 4-N-methylpyridine (Aldrich) and (3-chloropropyl)triethoxysilane. See reference [7] or the Supporting Information for details.
  • 52
    • 34447292189 scopus 로고    scopus 로고
    • Supplementary TEM images showing particle aggregates can be found in the Supporting Information
    • Supplementary TEM images showing particle aggregates can be found in the Supporting Information.
  • 56
    • 34447269766 scopus 로고    scopus 로고
    • Control reactions for the formation of 6, 10, 12, and 14 in the absence of 2 under otherwise identical conditions to those in Table 2 proceeded to 0, 0, 1, and 0% conversion respectively.
    • Control reactions for the formation of 6, 10, 12, and 14 in the absence of 2 under otherwise identical conditions to those in Table 2 proceeded to 0, 0, 1, and 0% conversion respectively.
  • 57
    • 34447291403 scopus 로고    scopus 로고
    • We have also found that an analogue of 2 prepared from the direct coupling of 1 with magnetite nanoparticles (without a silica layer) can serve as an active and recyclable acylation catalyst in the BOC protection of indole under conditions identical to those in Table 2, entries 7-9, In these experiments, 10 could be prepared from 9 in quantitative conversion in each of five consecutive cycles
    • We have also found that an analogue of 2 prepared from the direct coupling of 1 with magnetite nanoparticles (without a silica layer) can serve as an active and recyclable acylation catalyst in the BOC protection of indole (under conditions identical to those in Table 2, entries 7-9). In these experiments, 10 could be prepared from 9 in quantitative conversion in each of five consecutive cycles.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.