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Volumn 10, Issue 20, 2008, Pages 4673-4676

Potassium t-butoxide alone can promote the biaryl coupling of electron-deficient nitrogen heterocycles and haloarenes

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EID: 58449085051     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8019764     Document Type: Article
Times cited : (448)

References (49)
  • 1
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    • Beller, M, Bolm, C, Eds, Wiley-VCH: Weinheim
    • (a) Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 2004.
    • (2004) Transition Metals for Organic Synthesis
  • 3
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    • 2nd edition; de Meijere, A, Diederich, F, Eds, Wiley-VCH: Weinheim
    • (a) Metal-Catalyzed Cross-Coupling Reactions, 2nd edition; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
    • (2004) Metal-Catalyzed Cross-Coupling Reactions
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    • Cross-Coupling Reactions. Top. Curr. Chem.; Miyaura, N., Ed.; Springer: Berlin, 2002; 219.
    • (b) Cross-Coupling Reactions. Top. Curr. Chem.; Miyaura, N., Ed.; Springer: Berlin, 2002; Vol. 219.
  • 5
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    • For recent reviews on biaryl synthesis through C-H bond arylation of aromatic compounds, see: a
    • For recent reviews on biaryl synthesis through C-H bond arylation of aromatic compounds, see: (a) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
    • (2007) Chem. Rev , vol.107 , pp. 174
    • Alberico, D.1    Scott, M.E.2    Lautens, M.3
  • 12
    • 0034286415 scopus 로고    scopus 로고
    • In the metal-catalyzed direct C-H bond arylation chemistry, electron-deficient nitrogen heterocycles are still challenging substrates, a Mukhopadhyay, S, Rothenberg, G, Gitis, D, Baidossi, M, Ponde, D. E, Sasson, Y. J. Chem. Soc, Perkin Trans. 2 2000, 1809
    • In the metal-catalyzed direct C-H bond arylation chemistry, electron-deficient nitrogen heterocycles are still challenging substrates, (a) Mukhopadhyay, S.; Rothenberg, G.; Gitis, D.; Baidossi, M.; Ponde, D. E.; Sasson, Y. J. Chem. Soc., Perkin Trans. 2 2000, 1809.
  • 27
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    • Although we hold the temperature at 50 °C, this is the bulk temperature of the reaction mixture. As well documented, we assume that the reaction is taking place at high-temperature hotspots that are generated by microwave irradiation, For reviews on the use of microwave in organic synthesis, see: (a) de la Hoz, A, Díaz-Oritiz, Á, Moreno, A. Chem. Soc. Rev. 2005, 34, 164
    • Although we hold the temperature at 50 °C, this is the bulk temperature of the reaction mixture. As well documented, we assume that the reaction is taking place at high-temperature "hotspots" that are generated by microwave irradiation, For reviews on the use of microwave in organic synthesis, see: (a) de la Hoz, A.; Díaz-Oritiz, Á.; Moreno, A. Chem. Soc. Rev. 2005, 34, 164.
  • 29
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    • These results imply that our reaction does not proceed through aryne intermediates, although such a mechanism cannot be rigorously excluded at this stage, (a) Bates, R. B.; Janda, K. D. J. Org. Chem. 1982, 47, 4374.
    • These results imply that our reaction does not proceed through aryne intermediates, although such a mechanism cannot be rigorously excluded at this stage, (a) Bates, R. B.; Janda, K. D. J. Org. Chem. 1982, 47, 4374.
  • 32
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    • tBu similarly.
    • tBu similarly.
  • 33
    • 61349142326 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 34
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    • Renaud, P, Sibi, M. P, Eds, Wiley-VCH: Weinheim
    • Studer, A.; Bossart, M. Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, p 62.
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 62
    • Studer, A.1    Bossart, M.2
  • 38
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    • For the selected examples using t-butoxides and haloarenes in C-H bond arylation reactions, see: (a) Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404.
    • For the selected examples using t-butoxides and haloarenes in C-H bond arylation reactions, see: (a) Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404.
  • 40
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    • Reference 8
    • (c) Reference 8.
  • 48
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    • t-Butoxides are typical bases in the arylation of amines and alcohols using haloarenes. For a review, see: (a) Hang, L.; Buchwald, S. L. Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; Chapter 13.
    • t-Butoxides are typical bases in the arylation of amines and alcohols using haloarenes. For a review, see: (a) Hang, L.; Buchwald, S. L. Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; Chapter 13.
  • 49
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    • tBu-promoted) reactions, see: (b) Shi, L.; Wang, M.; Fan. C.-A.; Zhang, F.-M.; Tu, Y.-Q. Org. Lett. 2003, 5, 3515.
    • tBu-promoted) reactions, see: (b) Shi, L.; Wang, M.; Fan. C.-A.; Zhang, F.-M.; Tu, Y.-Q. Org. Lett. 2003, 5, 3515.


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