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Volumn 132, Issue 5, 2010, Pages 1464-1465

Visible-light photoredox catalysis: Aza-Henry reactions via C-H functionalization

Author keywords

[No Author keywords available]

Indexed keywords

ARYL AMINES; ATMOSPHERIC OXYGEN; AZA-HENRY REACTIONS; C-C BONDS; C-H FUNCTIONALIZATION; CHEMICAL EQUATIONS; EFFICIENT COUPLING; IMINIUM IONS; IN-SITU; IR(PPY); MECHANISTIC STUDIES; NITROALKANES; PHOTOREDOX CATALYSIS; RADICAL CATIONS; TERTIARY AMINE; VISIBLE LIGHT;

EID: 76149096852     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja909145y     Document Type: Article
Times cited : (745)

References (36)
  • 4
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    • 2+ and related complexes, see: (a) Kalyanasundaram, K. Coord. Chem. Rev. 1982, 46, 159.
    • 2+ and related complexes, see: (a) Kalyanasundaram, K. Coord. Chem. Rev. 1982, 46, 159.
  • 28
    • 1542287638 scopus 로고    scopus 로고
    • 6, see: Slinker, J. D.; Gorodetsky, A. A.; Lowry, M. S.; Wang, J.; Parker, S.; Rohl, R.; Bernhard, S.; Malliaras, G. G. J. Am. Chem. Soc. 2004, 126, 2763.
    • 6, see: Slinker, J. D.; Gorodetsky, A. A.; Lowry, M. S.; Wang, J.; Parker, S.; Rohl, R.; Bernhard, S.; Malliaras, G. G. J. Am. Chem. Soc. 2004, 126, 2763.
  • 30
    • 76149114419 scopus 로고    scopus 로고
    • See the Supporting Information for details
    • See the Supporting Information for details.
  • 31
    • 0037149057 scopus 로고    scopus 로고
    • N-Aryltetrahydroisoquinolines were prepared via Buchwald - Hartwig coupling (see: Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581).
    • N-Aryltetrahydroisoquinolines were prepared via Buchwald - Hartwig coupling (see: Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581).
  • 32
    • 70350662869 scopus 로고    scopus 로고
    • For an alternative approach to N-arylation, see
    • For an alternative approach to N-arylation, see: Barker, T. J.; Jarvo, E. R. J. Am. Chem. Soc. 2009, 131, 15598.
    • (2009) J. Am. Chem. Soc , vol.131 , pp. 15598
    • Barker, T.J.1    Jarvo, E.R.2
  • 33
    • 0000474999 scopus 로고    scopus 로고
    • An insightful reviewer suggested that this reaction may be mediated by singlet O2 sensitization by 4 see: Demas, J. N, Harris, E. W, McBride, R. P. J. Am. Chem. Soc. 1977, 99, 3547
    • 2 sensitization by 4 (see: Demas, J. N.; Harris, E. W.; McBride, R. P. J. Am. Chem. Soc. 1977, 99, 3547).
  • 34
    • 70349911749 scopus 로고    scopus 로고
    • 2-mediated oxidation of dibenzylamine to the corresponding imine (see: Jiang, G.; Chen, J.; Huang, J.-S.; Che, C.-M. Org. Lett. 2009, 11, 4568):
    • 2-mediated oxidation of dibenzylamine to the corresponding imine (see: Jiang, G.; Chen, J.; Huang, J.-S.; Che, C.-M. Org. Lett. 2009, 11, 4568):
  • 35
    • 76149146497 scopus 로고    scopus 로고
    • Using 4 under an oxygen atmosphere, we observed only 12% conversion of dibenzylamine to its imine after 12 h cf. TPP, O2, 10-14 h, In contrast, we found that TPP is capable of mediating the oxidative aza-Henry reaction of 1, but the reaction required 72 h for complete conversion compared with only 10 h under our conditions using 4. See the Supporting Information for further details
    • 2, 10-14 h). In contrast, we found that TPP is capable of mediating the oxidative aza-Henry reaction of 1, but the reaction required 72 h for complete conversion compared with only 10 h under our conditions using 4. See the Supporting Information for further details.
  • 36
    • 76149123338 scopus 로고    scopus 로고
    • 1H NMR analysis, but 12 was not stable under purification by chromatography.
    • 1H NMR analysis, but 12 was not stable under purification by chromatography.


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