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Volumn 132, Issue 29, 2010, Pages 9982-9983

Rh catalyzed olefination and vinylation of unactivated acetanilides

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST LOADINGS; CATALYTIC AMOUNTS; HECK COUPLING; OLEFINATION; PD CATALYST; TERMINAL OXIDANTS; VINYLATION;

EID: 77955797760     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja103834b     Document Type: Article
Times cited : (375)

References (52)
  • 1
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    • For lead references on Heck couplings, see: a, In, de Meijere, A., Diederich, F., Eds.; Wiley-VCH: New York
    • For lead references on Heck couplings, see: (a) Bräse, S.; de Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: New York, 2004; p 217.
    • (2004) Metal-Catalyzed Cross-Coupling Reactions , pp. 217
    • Bräse, S.1    De Meijere, A.2
  • 6
    • 0037048663 scopus 로고    scopus 로고
    • For use of oxidative C-H olefination reactions in natural product synthesis, see: a
    • For use of oxidative C-H olefination reactions in natural product synthesis, see: (a) Dangel, B. D.; Godula, K.; Youn, S. W.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2002, 124, 11856.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 11856
    • Dangel, B.D.1    Godula, K.2    Youn, S.W.3    Sezen, B.4    Sames, D.5
  • 37
    • 77955791662 scopus 로고    scopus 로고
    • See Supporting Information for further information
    • See Supporting Information for further information.
  • 38
    • 84855627320 scopus 로고    scopus 로고
    • 1H NMR of the crude products
    • 1H NMR of the crude products.
  • 39
    • 77955837050 scopus 로고    scopus 로고
    • Steric congestion near the acetanilide directing group slows down the reaction and deteriorates the yield
    • Steric congestion near the acetanilide directing group slows down the reaction and deteriorates the yield:
  • 40
    • 77955779338 scopus 로고    scopus 로고
    • Increasing the temperature or the catalytic loading did not significantly improve the yield in this case. However, no side products were observed
    • Increasing the temperature or the catalytic loading did not significantly improve the yield in this case. However, no side products were observed.
  • 41
    • 76249084575 scopus 로고    scopus 로고
    • For the application of a structurally related olefin-oxazoline ligand in Rh catalysis, see
    • For the application of a structurally related olefin-oxazoline ligand in Rh catalysis, see: Hahn, B. T.; Tewes, F.; Frohlich, R.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 1143.
    • (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 1143
    • Hahn, B.T.1    Tewes, F.2    Frohlich, R.3    Glorius, F.4
  • 42
    • 77955834162 scopus 로고    scopus 로고
    • high value of the TOF for the acrylate substrate is in accordance with previous reports on related transformations; see refs 2 and 3
    • The high value of the TOF for the acrylate substrate is in accordance with previous reports on related transformations; see refs 2 and 3.
  • 43
    • 77955831061 scopus 로고    scopus 로고
    • It should be noted that when 1-octene was engaged as a substrate, only trace amounts of product could be detected
    • It should be noted that when 1-octene was engaged as a substrate, only trace amounts of product could be detected.
  • 45
    • 73149124729 scopus 로고    scopus 로고
    • For direct catalytic C-H oxidative Heck coupling to ethylene, see
    • (b) Smith, C. R.; RajanBabu, T. V. Tetrahedron 2010, 66, 1102. For direct catalytic C-H oxidative Heck coupling to ethylene, see:
    • (2010) Tetrahedron. , vol.66 , pp. 1102
    • Smith, C.R.1    RajanBabu, T.V.2
  • 50
    • 0344006321 scopus 로고    scopus 로고
    • For two of the many types of transformations of terminal olefins, see reviews on Ru catalyzed olefin metathesis: a
    • For two of the many types of transformations of terminal olefins, see reviews on Ru catalyzed olefin metathesis: (a) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3012
    • Fürstner, A.1
  • 51
    • 3343012187 scopus 로고    scopus 로고
    • For an overview on Rh catalyzed hydroformylation, see
    • (b) Grubbs, R. H. Tetrahedron 2004, 60, 7117. For an overview on Rh catalyzed hydroformylation, see:
    • (2004) Tetrahedron. , vol.60 , pp. 7117
    • Grubbs, R.H.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.