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Volumn 48, Issue 6, 2007, Pages 1033-1035

Copper-catalyzed oxidative esterification of alcohols with aldehydes activated by Lewis acids

Author keywords

C H Transformation; Copper; Indium; Oxidative esterification

Indexed keywords

ALCOHOL; ALDEHYDE; BROMINE DERIVATIVE; COPPER; HYDROPEROXIDE DERIVATIVE; LEWIS ACID; OXIDIZING AGENT; WATER;

EID: 33846263996     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.169     Document Type: Article
Times cited : (113)

References (32)
  • 27
    • 0003916055 scopus 로고
    • Both Cu(I) and Cu(II) salts were viable catalysts for the oxidative esterification reaction. However, the oxidation state of the active catalyst species cannot be predicted due to the ability of Cu(I) salts to oxidatively, and Cu(II) salts to reductively decompose peresters to generate radicals. See:, Academic Press, New York
    • Both Cu(I) and Cu(II) salts were viable catalysts for the oxidative esterification reaction. However, the oxidation state of the active catalyst species cannot be predicted due to the ability of Cu(I) salts to oxidatively, and Cu(II) salts to reductively decompose peresters to generate radicals. See:. Sheldon R.A., and Kochi J.K. Metal-catalyzed Oxidation of Organic Compounds (1981), Academic Press, New York
    • (1981) Metal-catalyzed Oxidation of Organic Compounds
    • Sheldon, R.A.1    Kochi, J.K.2
  • 28
    • 33846233596 scopus 로고    scopus 로고
    • note
    • 10 The crude reaction mixture was purified by column chromatography (EtOAc-hexanes mixtures) to provide the esters 3a-k.
  • 29
    • 0034706037 scopus 로고    scopus 로고
    • The oxidation of the hemiacetal intermediate 4 likely occurs through a radical mechanism since radical scavenger, 2,6-di-tert-butyl-4-methyl phenol (BHT) inhibits the reaction. Radical based mechanisms have been proposed for the oxidation of alcohols to aldehydes by galactose oxidases. For recent mechanstic studies, see:
    • The oxidation of the hemiacetal intermediate 4 likely occurs through a radical mechanism since radical scavenger, 2,6-di-tert-butyl-4-methyl phenol (BHT) inhibits the reaction. Radical based mechanisms have been proposed for the oxidation of alcohols to aldehydes by galactose oxidases. For recent mechanstic studies, see:. Himo F., Eriksson L.A., Maseas F., and Siegbahn P.E.M. J. Am. Chem. Soc. 122 (2000) 8031
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 8031
    • Himo, F.1    Eriksson, L.A.2    Maseas, F.3    Siegbahn, P.E.M.4
  • 32
    • 33846237905 scopus 로고    scopus 로고
    • note
    • While no explosions were experienced during the synthesis of the esters reported in this letter, great care should always be exercised when handling peroxides in the presence of metal salts and high temperatures.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.