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Volumn 48, Issue 52, 2007, Pages 9096-9099

Aerobic oxidation under visible light irradiation of a fluorescent lamp with a combination of carbon tetrabromide and triphenyl phosphine

Author keywords

Aerobic oxidation; Carbon tetrabromide; Fluorescent lamp; Triphenylphosphine; Visible light

Indexed keywords

ALCOHOL; BENZYL ALCOHOL; BROMINE DERIVATIVE; CARBON TETRABROMIDE; CARBOXYLIC ACID; METHYL GROUP; PHOSPHINE DERIVATIVE; TRIPHENYL PHOSPHINE; UNCLASSIFIED DRUG;

EID: 36448938686     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.132     Document Type: Article
Times cited : (40)

References (39)
  • 2
    • 1642561828 scopus 로고    scopus 로고
    • For recent examples of oxidation of alcohols to the corresponding carboxylic acids with molecular oxygen, see:
    • For recent examples of oxidation of alcohols to the corresponding carboxylic acids with molecular oxygen, see:. Figiel P.J., Sobczak J.M., and Ziolkowski J.J. Chem. Commun. (2004) 244-245
    • (2004) Chem. Commun. , pp. 244-245
    • Figiel, P.J.1    Sobczak, J.M.2    Ziolkowski, J.J.3
  • 12
    • 33646546677 scopus 로고    scopus 로고
    • For recent examples of oxidation of alcohols to the corresponding aldehydes with molecular oxygen, see:
    • For recent examples of oxidation of alcohols to the corresponding aldehydes with molecular oxygen, see:. Ohkubo K., Suga K., and Fukuzumi S. Chem. Commun. (2006) 2018-2020
    • (2006) Chem. Commun. , pp. 2018-2020
    • Ohkubo, K.1    Suga, K.2    Fukuzumi, S.3
  • 19
    • 4143153074 scopus 로고    scopus 로고
    • and references cited therein
    • Stahl S.S. Angew. Chem., Int. Ed. 43 (2004) 3400-3420 and references cited therein
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3400-3420
    • Stahl, S.S.1
  • 29
    • 36448937258 scopus 로고    scopus 로고
    • note
    • Among our study, acetonitrile was a suitable solvent for alcohols and ethyl acetate was suitable for a methyl group at the aromatic nucleus, respectively, see Supplementary data.
  • 30
    • 36448996818 scopus 로고    scopus 로고
    • note
    • The radical species of secondary alcohols are, in general, generated easier than that of primary ones. Unfortunately, we do not have any direct data to explain this result, and the study is now in progress in our laboratory.
  • 31
    • 36448955532 scopus 로고    scopus 로고
    • note
    • Since transesterification of the substrate alcohols occurred when using ethyl acetate as solvent, we generally used acetonitrile when using alcohols as substrates and ethyl acetate when using aromatic methyl group as substrates.
  • 32
    • 36448934667 scopus 로고    scopus 로고
    • note
    • We also examined with 4-methyl benzyl alcohol to study the selectivity between alcohol and methyl group, and we could obtain 4-methylbenzoic acid in 60% yield as the main product. Alcohol is relatively easily oxidized than methyl group; however, the selectivity is not so clear.
  • 33
    • 36448929600 scopus 로고    scopus 로고
    • note
    • Only 19% of 2 was obtained.
  • 34
    • 36448959920 scopus 로고    scopus 로고
    • note
    • Although we examined this reaction with 3-methylpyrrole as test substrate, the complex mixture was obtained instead of the corresponding carboxylic acid.
  • 35
    • 36448968398 scopus 로고    scopus 로고
    • note
    • The reaction is thought to proceed through an aldehyde as an intermediate since 2 was obtained in 88% yield when benzaldehyde was subjected to the same aerobic photo-oxidation conditions.
  • 39
    • 36448980090 scopus 로고    scopus 로고
    • note
    • This oxidation method is also applicable to mol scale conditions, and 4, for example, was obtained in 77% yield when using 24 as substrate under similar conditions mentioned above.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.