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Volumn 71, Issue 15, 2006, Pages 5440-5447

Reconstructed hydrotalcite as a highly active heterogeneous base catalyst for carbon-carbon bond formations in the presence of water

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM; CHEMICAL BONDS; MAGNESIA; NITRILE RESINS; OXIDES; REACTION KINETICS;

EID: 33746439483     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060345l     Document Type: Article
Times cited : (160)

References (98)
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    • (1997) Organic Reactions in Aqueous Media
    • Li, C.-J.1    Chan, T.-H.2
  • 51
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    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • (a) Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 139.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 139
    • Heathcock, C.H.1
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    • Mahrwald, R., Ed.; Wiley-VCH; Weinheim, Germany
    • (c) Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH; Weinheim, Germany, 2004.
    • (2004) Modern Aldol Reactions
  • 77
    • 33746407800 scopus 로고    scopus 로고
    • note
    • 4+-mont catalyst exclusively afforded 3-hydroxy-2-methylpentanal as an aldol product of propionaldehyde.
  • 78
    • 33746408263 scopus 로고    scopus 로고
    • note
    • The amount of water as a solvent is a crucial factor for the catalytic activity of the reconstructed HT. The yield of 2 gradually decreased with increasing amount of water: 78% (1 mL), 70% (2 mL), and 25% (3 mL).
  • 79
    • 33746434991 scopus 로고    scopus 로고
    • note
    • In the 100 mmol scale aldol reaction of n-butyraldehyde using the reconstructed HT, the following reactivity of surfactants was observed: DTMAB (90) > sodium dodecyl sulfate (35) > Triton X 100 (13) > non (8). The values in parentheses are yields of 1,1-dimethoxy-2-ethyl-3-hexanol. Without the reconstructed HT catalyst, the aldolization did not occur even in the presence of DTMAB.
  • 82
    • 0003417469 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • (b) Jung, M. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4.
    • (1991) Comprehensive Organic Synthesis , vol.4
    • Jung, M.E.1
  • 87
    • 0038998967 scopus 로고    scopus 로고
    • The Knoevenagel reaction of malononitrile with benzaldehyde without any catalyst in the presence of water has been reported. See: Bigi, F.; Conforti, M. L.; Maggi, R.; Piccinno, A.; Sartori, G. Green Chem. 2000, 2, 101. Under our reaction conditions, the reaction of malononitrile with benzaldehyde gave 82% of the corresponding product.
    • (2000) Green Chem. , vol.2 , pp. 101
    • Bigi, F.1    Conforti, M.L.2    Maggi, R.3    Piccinno, A.4    Sartori, G.5
  • 89
    • 33746400673 scopus 로고    scopus 로고
    • note
    • An excess acceptor was used to avoid the Michael reaction.
  • 91
    • 33746445077 scopus 로고    scopus 로고
    • note
    • Ethyl cyanoacetate also reacted with 2-cyclohexen-1-one to afford the 1,4-addition product selectively. However, the yield of the Michael product was lower than 50%.
  • 94
    • 0005032017 scopus 로고
    • Benzalacetone is formed by base-catalyzed condensation of 2,4-pentanedione with benzaldehyde followed by deacylation. See: Tsuboi, S.; Uno, T.; Takeda, A. Chem. Lett. 1978, 1325.
    • (1978) Chem. Lett. , pp. 1325
    • Tsuboi, S.1    Uno, T.2    Takeda, A.3
  • 95
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    • note
    • - groups are indistinguishable. We think that the identical basicity of the HTs prepared by different methods may arise from the evacuation and/or exposure of the hydrated HTs to air before the condensation reaction.
  • 97
    • 33746408736 scopus 로고    scopus 로고
    • note
    • 2c


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.