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Volumn 74, Issue 11, 2009, Pages 4272-4277

Copper-catalyzed synthesis of benzoxazoles via a regioselective C-H functionalization/C-O bond formation under an air atmosphere

Author keywords

[No Author keywords available]

Indexed keywords

AIR ATMOSPHERE; BOND FORMATION; CATALYTIC SYNTHESIS; CATALYZED SYNTHESIS; CHEMICAL EQUATIONS; DICHLOROBENZENE; EFFICIENT METHOD; FUNCTIONALIZED; META POSITIONS; MILD REACTION CONDITIONS; REGIO-SELECTIVE; TERMINAL OXIDANTS;

EID: 66249113169     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900513z     Document Type: Article
Times cited : (183)

References (66)
  • 56
    • 33744786786 scopus 로고    scopus 로고
    • For relevant copper-mediated C-H functionalization, see:
    • For relevant copper-mediated C-H functionalization, see: (a) Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 6790
    • Chen, X.1    Hao, X.-S.2    Goodhue, C.E.3    Yu, J.-Q.4
  • 58
    • 51549113576 scopus 로고    scopus 로고
    • For intramolecular hydroarylation of alkenes by directed aromatic C-H functionalization/C-C bond formation, see:
    • For intramolecular hydroarylation of alkenes by directed aromatic C-H functionalization/C-C bond formation, see: (a) Harada, H.; Thalji, R. K.; Bergman, R. G.; Ellman, J. A. J. Org. Chem. 2008, 73, 6772.
    • (2008) J. Org. Chem. , vol.73 , pp. 6772
    • Harada, H.1    Thalji, R.K.2    Bergman, R.G.3    Ellman, J.A.4
  • 61
    • 66249107296 scopus 로고    scopus 로고
    • Reaction of 3k in o-DCB at 110°C resulted in incomplete reaction and 4k was obtained in 24% yield with a trace amount of chlorinated byproduct. The formation of chlorinated byproduct was not observed for the reaction of other substrates
    • Reaction of 3k in o-DCB at 110°C resulted in incomplete reaction and 4k was obtained in 24% yield with a trace amount of chlorinated byproduct. The formation of chlorinated byproduct was not observed for the reaction of other substrates.
  • 64
    • 0141923586 scopus 로고    scopus 로고
    • We have reported in our previous communication that no kinetic isotope effect was observed in an intramolecular competition experiment using ortho deuterium labeled substrate (see ref 22). This suggests that a hydrogen abstraction step is not involved in the rate determining step and other metalation mechanisms such as σ-bond metathesis might be eliminated. Intramolecular isotope effects are sometimes observed in palladium-catalyzed C-H functionalizations, see:
    • We have reported in our previous communication that no kinetic isotope effect was observed in an intramolecular competition experiment using ortho deuterium labeled substrate (see ref 22). This suggests that a hydrogen abstraction step is not involved in the rate determining step and other metalation mechanisms such as σ-bond metathesis might be eliminated. Intramolecular isotope effects are sometimes observed in palladium-catalyzed C-H functionalizations, see: (a) Hennessy, E. J.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 12084.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 12084
    • Hennessy, E.J.1    Buchwald, S.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.