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Volumn 47, Issue 48, 2008, Pages 9330-9333

Efficient aerobic oxidative synthesis of 2-substituted benzoxazoles, benzothiazoles, and benzimidazoles catalyzed by 4-Methoxy-TEMPO

Author keywords

Aerobic oxidation; Cyclization; Heterocycles; Synthetic methods

Indexed keywords

CHEMICAL REACTIONS; FREE RADICALS;

EID: 56449089532     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200803381     Document Type: Article
Times cited : (340)

References (41)
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    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 4790-4796
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    • Angew. Chem. Int. Ed. 2008, 47, 3506-3523.
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 3506-3523
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    • For examples in medicinal chemistry, see: a
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    • McKee, M.L.1    Kerwin, S.M.2
  • 36
    • 0037120130 scopus 로고    scopus 로고
    • It is well known that two kinds of resonance structures for TEMPO exist (I and II). The structures result from the unpaired electron delocalized between the nitrogen and the oxygen atoms. The greater the solvent polarity, the more favored structure II will be, as it has the larger electron density on the oxygen atom and spin density on the nitrogen atom. Structure II should reduce the hydrogen abstraction reactivity of TEMPO with phenols. Otherwise, the hydrogen-bonding interaction of TEMPO with protic solvents should disturb the interaction between TEMPO and phenols. See: a) P. Franchi, M. Marco Lucarini, P. Pedrielli, G. F. Pedulli, ChemPhysChem 2002, 3, 789-793, and references therein;
    • It is well known that two kinds of resonance structures for TEMPO exist (I and II). The structures result from the unpaired electron delocalized between the nitrogen and the oxygen atoms. The greater the solvent polarity, the more favored structure II will be, as it has the larger electron density on the oxygen atom and spin density on the nitrogen atom. Structure II should reduce the hydrogen abstraction reactivity of TEMPO with phenols. Otherwise, the hydrogen-bonding interaction of TEMPO with protic solvents should disturb the interaction between TEMPO and phenols. See: a) P. Franchi, M. Marco Lucarini, P. Pedrielli, G. F. Pedulli, ChemPhysChem 2002, 3, 789-793, and references therein;
  • 37
    • 0033532940 scopus 로고    scopus 로고
    • Chem. Soc, Chemical Equation Presented
    • b) L. R. C. Barclay, C. E. Edwards, M. R. Vinqvist, J. Am. Chem. Soc. 1999, 121, 6226-6231. (Chemical Equation Presented)
    • (1999) J. Am , vol.121 , pp. 6226-6231
    • Barclay, L.R.C.1    Edwards, C.E.2    Vinqvist, M.R.3
  • 38
    • 0003627253 scopus 로고    scopus 로고
    • The intermolecular hydrogen-bonding interaction between TEMPO and phenol has been studied both in solution and solid state. For solution studies, see: a I. G. Shenderovich, Z. Kecki, I. Wawer, G. S. Denisov, Spectrosc. Lett. 1997, 30, 1515-1523;
    • The intermolecular hydrogen-bonding interaction between TEMPO and phenol has been studied both in solution and solid state. For solution studies, see: a) I. G. Shenderovich, Z. Kecki, I. Wawer, G. S. Denisov, Spectrosc. Lett. 1997, 30, 1515-1523;
  • 39
    • 0035913772 scopus 로고    scopus 로고
    • for solid-state studies the single crystal structure of TEMPO·phenol adduct was obtained, see: b B. Ahrens, M. G. Davidson, V. T. Forsyth, M. F. Mahon, A. L. Johnson, S. A. Mason, R. D. Price, P. R. Raithby, J. Am. Chem. Soc. 2001, 123, 9164-9165.
    • for solid-state studies the single crystal structure of TEMPO·phenol adduct was obtained, see: b) B. Ahrens, M. G. Davidson, V. T. Forsyth, M. F. Mahon, A. L. Johnson, S. A. Mason, R. D. Price, P. R. Raithby, J. Am. Chem. Soc. 2001, 123, 9164-9165.
  • 40
    • 0344944928 scopus 로고    scopus 로고
    • For the hydrogen absraction between TEMPO and phenols, see: a
    • For the hydrogen absraction between TEMPO and phenols, see: a) C. Aliaga, A. Aspée, J. C. Scaiano, Org. Lett. 2003, 5, 4145-4148;
    • (2003) Org. Lett , vol.5 , pp. 4145-4148
    • Aliaga, C.1    Aspée, A.2    Scaiano, J.C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.