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Volumn 130, Issue 48, 2008, Pages 16184-16186

Oxidative Pd(II)-catalyzed C-H bond amination to carbazole at ambient temperature

Author keywords

[No Author keywords available]

Indexed keywords

CARBAZOLE DERIVATIVE; CARBON; HYDROGEN; PALLADIUM;

EID: 57149106741     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja806543s     Document Type: Article
Times cited : (518)

References (53)
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    • For recent examples, see: (a) Liegault, Lee, D.; Huestis, M. P.; Stuart, D. R.; Fagnou, K. J. Org. Chem. 2008, 73, 5022.
    • For recent examples, see: (a) Liegault, Lee, D.; Huestis, M. P.; Stuart, D. R.; Fagnou, K. J. Org. Chem. 2008, 73, 5022.
  • 14
  • 18
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    • C-H amination via nitrenes: (a) Espino, C. G.; Fiori, K. W.; Kim, M.; Du Bois, J. J. Am. Chem. Soc. 2004, 126, 15378, and references therein.
    • C-H amination via nitrenes: (a) Espino, C. G.; Fiori, K. W.; Kim, M.; Du Bois, J. J. Am. Chem. Soc. 2004, 126, 15378, and references therein.
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    • For examples of allylic C-H animations see: (g) Reed, S. A, White, M. C. J. Am. Chem. Soc. 2008, 130, 3316
    • For examples of allylic C-H animations see: (g) Reed, S. A.; White, M. C. J. Am. Chem. Soc. 2008, 130, 3316.
  • 33
    • 21944441002 scopus 로고    scopus 로고
    • and references therein. For a recent review on palladacycles see
    • For a recent review on palladacycles see Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527, and references therein.
    • (2005) Chem. Rev , vol.105 , pp. 2527
    • Dupont, J.1    Consorti, C.S.2    Spencer, J.3
  • 34
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    • For selected examples of reductive elimination of C-heteroatom bonds from Pd(IV), see: (a) Furuya, T.; Ritter, T. J. Am. Chem. Soc. 2008, 130, 10060.
    • (a) For selected examples of reductive elimination of C-heteroatom bonds from Pd(IV), see: (a) Furuya, T.; Ritter, T. J. Am. Chem. Soc. 2008, 130, 10060.
  • 39
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    • For reductive elimination from Pt(IV), see: (f) Pawlikowski, A. V.; Getty, A. D.; Goldberg, K. I. J. Am. Chem. Soc. 2007, 129, 10382.
    • For reductive elimination from Pt(IV), see: (f) Pawlikowski, A. V.; Getty, A. D.; Goldberg, K. I. J. Am. Chem. Soc. 2007, 129, 10382.
  • 40
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    • 2. (c) AcOH improved yield of 2.
    • 2. (c) AcOH improved yield of 2.
  • 41
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    • For electrophilic mechanism examples, see: a
    • For electrophilic mechanism examples, see: (a) Parshall, G. W. Acc. Chem. Res. 1970, 3, 139.
    • (1970) Acc. Chem. Res , vol.3 , pp. 139
    • Parshall, G.W.1
  • 47
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    • Davies, D. L.; Donald, S. M. A.; Macgregor, S. A J. Am. Chem. Soc. 2005, 127, 13754.
    • (b) Davies, D. L.; Donald, S. M. A.; Macgregor, S. A J. Am. Chem. Soc. 2005, 127, 13754.
  • 48
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    • For the monodeuterioamine d-1a we observed a kinetic isotope effect of 2.27; see Supporting Information for details.
    • For the monodeuterioamine d-1a we observed a kinetic isotope effect of 2.27; see Supporting Information for details.
  • 53
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    • We do not believe that this reaction proceeds through a directed Pd(II)-catalyzed iodination, followed by amination of the C-I bond. See, Mei, T.-S, Giri, R, Maugel, N, Yu, J.-Q. Angew. Chem, Int. Ed. 2008, 47, 6452. Treatment of the corresponding iodo-biphenyl amine (1o) under the oxidative Pd(II) conditions affords the same product, 2o, as seen in the tandem reaction
    • We do not believe that this reaction proceeds through a directed Pd(II)-catalyzed iodination, followed by amination of the C-I bond. See : Mei, T.-S.; Giri, R.; Maugel, N.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 6452. Treatment of the corresponding iodo-biphenyl amine (1o) under the oxidative Pd(II) conditions affords the same product, 2o, as seen in the tandem reaction.


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