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Volumn 12, Issue 23, 2010, Pages 5430-5433

Rh(III)-catalyzed tandem oxidative olefination-michael reactions between aryl carboxamides and alkenes

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EID: 78650375862     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102241f     Document Type: Article
Times cited : (266)

References (54)
  • 3
    • 0037048663 scopus 로고    scopus 로고
    • For the applications of oxidative Heck reactions in natural product synthesis, see
    • For the applications of oxidative Heck reactions in natural product synthesis, see: 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
  • 52
    • 78650333788 scopus 로고    scopus 로고
    • 5C(O)NHPh) in equimolar ratios in the absence of acrylate resulted in scrambling of deuterium into the ortho sites of both benzamides, which indicates that the ortho C-H activation here is a reversible process. See ref 12
    • 5C(O)NHPh) in equimolar ratios in the absence of acrylate resulted in scrambling of deuterium into the ortho sites of both benzamides, which indicates that the ortho C-H activation here is a reversible process. See ref 12.
  • 53
    • 78650342479 scopus 로고    scopus 로고
    • Nitrogen coordination in benzamide substrates has been recently proposed in related coupling reactions. See ref 10d
    • Nitrogen coordination in benzamide substrates has been recently proposed in related coupling reactions. See ref 10d.
  • 54
    • 78650361297 scopus 로고    scopus 로고
    • The methyl group in PhC(O)NHMe makes the amide oxygen more coordinating and should make amide oxygen a stronger chelator, favoring oxygen-directed C-H cleavage if oxygen metalation is followed. However, this does not seem to be consistent with the experimental results
    • The methyl group in PhC(O)NHMe makes the amide oxygen more coordinating and should make amide oxygen a stronger chelator, favoring oxygen-directed C-H cleavage if oxygen metalation is followed. However, this does not seem to be consistent with the experimental results.


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