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Volumn 74, Issue 17, 2009, Pages 6867-6869

An efficient catalyst system for Pd-catalyzed amination of [2.2]paracyclophanyl bromides

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; EFFICIENT CATALYSTS;

EID: 69549133800     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901310a     Document Type: Article
Times cited : (28)

References (53)
  • 20
    • 3142722640 scopus 로고    scopus 로고
    • (e) Dahmen, S. Org. Lett. 2004, 13, 2113-2116.
    • (2004) Org. Lett. , vol.13 , pp. 2113-2116
    • Dahmen, S.1
  • 39
    • 0032541260 scopus 로고    scopus 로고
    • For recent reviews on palladium-catalyzed aryl amination, see
    • For recent reviews on palladium-catalyzed aryl amination, see: (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2046-2067
    • Hartwig, J.F.1
  • 40
    • 0008842650 scopus 로고    scopus 로고
    • Ricci, A., Ed.; Wiley-VCH:Weinheim, Germany
    • (b) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH:Weinheim, Germany, 2000; p 195.
    • (2000) Modern Amination Methods , pp. 195
    • Hartwig, J.F.1
  • 52
    • 69549100134 scopus 로고    scopus 로고
    • note
    • In general, the rates for amination of bromobenzene, 1-bromonaphthalene, and 3-bromopyridine were faster than those for amination of brominated [2.2]paracyclophanes. The reaction of 3-bromopyridine with benzhydrylideneamine in toluene occurred to completion after 2 h at 110 °C in 96% yield with the catalytic system (0.5% Pd-DPPF and 0.5% 3a). Under the same reaction condition, reaction of benzhydrylideneamine with bromobenzene and 1-bromonaphthalene occurred to completion in 93% and 94% yield within only 3 and 5 h.


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