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Volumn 133, Issue 8, 2011, Pages 2350-2353

Rh(III)-catalyzed Directed C-H Olefination using an oxidizing directing group: Mild, efficient, and versatile

Author keywords

[No Author keywords available]

Indexed keywords

CH-BOND ACTIVATION; OLEFINATION; SELECTIVE FORMATION; YIELDING PROCESS;

EID: 79951846441     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja109676d     Document Type: Article
Times cited : (676)

References (56)
  • 3
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    • Recent reviews on C-H functionalization using transition metals: Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
    • (2010) Chem. Rev. , vol.110 , pp. 1147
    • Lyons, T.W.1    Sanford, M.S.2
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    • 79951864896 scopus 로고    scopus 로고
    • 101002/anie201007241
    • For a recent minireview, see: Patureau, F.; Glorius, F. Angew. Chem., Int. Ed. 2011, 10.1002/anie.201007241 It is interesting to note that, whereas the term "external oxidant" seems to be unambiguous, the term "internal oxidant" can either mean simply that one of the substrates acts as an oxidation equivalent or, in a more limited usage, that the catalyst gets oxidized internally before, at, or after the reaction event. For example, the halide group of aryl halides represents a truly internal oxidant in reactions like the Heck reaction.
    • (2011) Angew. Chem., Int. Ed.
    • Patureau, F.1    Glorius, F.2
  • 40
    • 77952570693 scopus 로고    scopus 로고
    • Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908. For the pioneering use of O -methyl hydroxamic acids (CONH(OMe)) as DG in C-H activation chemistry, see
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 6908
    • Guimond, N.1    Gouliaras, C.2    Fagnou, K.3
  • 43
    • 79952266875 scopus 로고    scopus 로고
    • Interestingly, using N -hydroxybenzamide as substrate, 72% of product 3aa was obtained.
    • Interestingly, using N -hydroxybenzamide as substrate, 72% of product 3aa was obtained.
  • 44
    • 79952268947 scopus 로고    scopus 로고
    • See Supporting Information for further details.
    • See Supporting Information for further details.
  • 45
    • 79952263596 scopus 로고    scopus 로고
    • No dehalogenation or demethoxylation was observed.
    • No dehalogenation or demethoxylation was observed.
  • 46
    • 79952272985 scopus 로고    scopus 로고
    • 1H NMR).
    • 1H NMR).
  • 47
    • 77949801096 scopus 로고    scopus 로고
    • In Pd(II)-catalyzed oxidative Heck reactions, the amide group is known for this kind of attack: Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3680 Indeed, under our standard reaction conditions, we have also observed the five-membered lactam side product.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 3680
    • Wasa, M.1    Engle, K.M.2    Yu, J.-Q.3
  • 48
    • 43449134102 scopus 로고    scopus 로고
    • For recent direct catalytic C-H oxidative Heck couplings to ethylene, see: Kormos, C. M.; Leadbeater, N. E. J. Org. Chem. 2008, 73, 3854
    • (2008) J. Org. Chem. , vol.73 , pp. 3854
    • Kormos, C.M.1    Leadbeater, N.E.2
  • 54
    • 79952272626 scopus 로고    scopus 로고
    • V species could be invoked.
    • V species could be invoked.
  • 56
    • 79952268948 scopus 로고    scopus 로고
    • 1H NMR or GC-MS of the crude reaction mixture. See Supporting Information for further details.
    • 1H NMR or GC-MS of the crude reaction mixture. See Supporting Information for further details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.