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Volumn 72, Issue 6, 2007, Pages 2143-2150

Novel Pd/C-catalyzed redox reactions between aliphatic secondary alcohols and ketones under hydrogenation conditions: Application to H-D exchange reaction and the mechanistic study

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; HYDROGENATION; KETONES; PALLADIUM; REACTION KINETICS; REDOX REACTIONS;

EID: 33947230753     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062582u     Document Type: Article
Times cited : (60)

References (56)
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    • (2003) Chem., Int. Ed , vol.42 , pp. 2892-2895
    • Angew1
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    • 33947257054 scopus 로고    scopus 로고
    • Selected review, see:, 2nd ed, Wiley-VCH: New York
    • Selected review, see: Larock, R. C. In Comprehensive Organic Chemistry, 2nd ed.; Wiley-VCH: New York, 1999.
    • (1999) Comprehensive Organic Chemistry
    • Larock, R.C.1
  • 38
    • 0001040853 scopus 로고    scopus 로고
    • Ru(II) complex-catalyzed hydrogenation of ketones to alcohols was pioneeringly reported by Noyori et al. See: Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562-7563.
    • Ru(II) complex-catalyzed hydrogenation of ketones to alcohols was pioneeringly reported by Noyori et al. See: Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562-7563.
  • 47
    • 0002121370 scopus 로고
    • Selected reviews, see: a, Trost, B. M, Fleming, I, Eds, Pergamon: Oxford
    • Selected reviews, see: (a) Kellogg, R. M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 8, pp 79-106.
    • (1991) Comprehensive Organic Synthesis , vol.8 , pp. 79-106
    • Kellogg, R.M.1
  • 49
    • 0037807002 scopus 로고    scopus 로고
    • Burwell and co-workers have studied the vapor-phase interchange reactions accompanied by hydrogenation and dehydrogenation occurring upon passage of the vapor of a secondary alcohol-ketone mixture using H2 as a carrier gas over various metal catalysts; see: (a) Newham, J, Burwell, R. L, Jr. J. Am. Chem. Soc. 1964, 86, 1179-1186
    • 2 as a carrier gas over various metal catalysts; see: (a) Newham, J.; Burwell, R. L., Jr. J. Am. Chem. Soc. 1964, 86, 1179-1186.
  • 51
    • 33947278011 scopus 로고    scopus 로고
    • Although suspicions are raised about the effect of the contaminated acid in the catalyst21 toward the reduction of 2-decanone (4, the acidity of the catalyst (Pd/C, Rh/C, or Pt/C) did not correlate with the present redox reaction see the Supporting Information
    • 21 toward the reduction of 2-decanone (4), the acidity of the catalyst (Pd/C, Rh/C, or Pt/C) did not correlate with the present redox reaction (see the Supporting Information).
  • 52
    • 33747052880 scopus 로고    scopus 로고
    • Derdau and Atzrodt reported the deuteration at the benzylic position of the optically active 1-phenylbutan-1-ols using the Pd/C-NaBD4-D 2O system was accompanied by racemization; see: Derdau, V, Atzrodt, J. Synlett 2006, 1918-1922. We also observed racemization during the deuteration of L-phenylalanine; please see ref 13
    • 2O system was accompanied by racemization; see: Derdau, V.; Atzrodt, J. Synlett 2006, 1918-1922. We also observed racemization during the deuteration of L-phenylalanine; please see ref 13.


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