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Volumn 13, Issue 8, 2011, Pages 2134-2137

Pd(II)-catalyzed intramolecular amidoarylation of alkenes with molecular oxygen as sole oxidant

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EID: 79955390732     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2006083     Document Type: Article
Times cited : (66)

References (62)
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    • For difunctionalization of alkenes using oxygen as sole oxidant
    • For difunctionalization of alkenes using oxygen as sole oxidant: Zhu, M.-K.; Zhao, J.-F.; Loh, T.-P. J. Am. Chem. Soc. 2010, 132, 6284.
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    • For overviews on pyrrolizidines
    • For overviews on pyrrolizidines, see: Liddell, J. R. Nat. Prod. Rep. 2002, 19, 773.
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    • Liddell, J.R.1
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    • For recent studies on syn-aminopalladation
    • For recent studies on syn-aminopalladation, see: Neukom, J. D.; Perch, N. S.; Wolfe, J. P. J. Am. Chem. Soc. 2010, 132, 6276.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 6276
    • Neukom, J.D.1    Perch, N.S.2    Wolfe, J.P.3
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    • 0021494516 scopus 로고
    • For examples of anti-aminopalladation, see ref 7a and Å
    • For examples of anti-aminopalladation, see ref 7a and Å kermark, B.; Zetterberg, K. J. Am. Chem. Soc. 1984, 106, 5560.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 5560
    • Kermark, B.1    Zetterberg, K.2
  • 59
    • 48749120080 scopus 로고    scopus 로고
    • An alternative mechanism involving sequential C-H bond activation/carbopalladation of alkene/C-N bond formation is unlikely in our system because the bimolecular palladation of arenes is often assisted by protic acids. For example, see: ref 13d and
    • An alternative mechanism involving sequential C-H bond activation/carbopalladation of alkene/C-N bond formation is unlikely in our system because the bimolecular palladation of arenes is often assisted by protic acids. For example, see: ref 13d and Houlden, C. E.; Bailey, C. D.; Ford, J. G.; Gagné, M. R.; Lloyd-Jones, G. C.; Booker- Milburn, K. I. J. Am. Chem. Soc. 2008, 130, 10066.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 10066
    • Houlden, C.E.1    Bailey, C.D.2    Ford, J.G.3    Gagné, M.R.4    Lloyd-Jones, G.C.5    Booker-Milburn, K.I.6
  • 60
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    • In additon, successful oxidative triple cyclization (Scheme 3) also rules out this mechanism. We thank the reviewer for pointing out this possibility
    • In additon, successful oxidative triple cyclization (Scheme 3) also rules out this mechanism. We thank the reviewer for pointing out this possibility.
  • 61
    • 34047161855 scopus 로고    scopus 로고
    • Termination with hydride elimination is characteristic of an oxidative amination of alkene under a Pd0/PdII catalytic cycle. For recent reviews
    • Termination with hydride elimination is characteristic of an oxidative amination of alkene under a Pd0/PdII catalytic cycle. For recent reviews Kotov V., Scarborough C.C., Stahl S.S. Inorg. Chem. 2007, 46, 1910.
    • (2007) Inorg. Chem. , vol.46 , pp. 1910
    • Kotov, V.1    Scarborough, C.C.2    Stahl, S.S.3


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