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Volumn 9, Issue 9, 2007, Pages 1781-1783

Synthesis of biaryls via decarboxylative Pd-catalyzed cross-coupling reaction

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EID: 34248384892     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070495y     Document Type: Article
Times cited : (205)

References (39)
  • 4
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    • Suzuki, A, Diederich, F, Stang, P. J, Eds, Wiley-VHC: Weinheim, Germany
    • (d) Metal-Catalyzed Cross-Coupling Reactions; Suzuki, A., Diederich, F., Stang, P. J., Eds.; Wiley-VHC: Weinheim, Germany, 1998.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions
  • 6
    • 85065137145 scopus 로고    scopus 로고
    • Other powerful transition-metal-catalyzed-synthetic methods for the preparation of biaryls are available, a For Cu-catalyzed cross-coupling reactions, see: Fanta, P. E. Synthesis 1974, 9
    • Other powerful transition-metal-catalyzed-synthetic methods for the preparation of biaryls are available, (a) For Cu-catalyzed cross-coupling reactions, see: Fanta, P. E. Synthesis 1974, 9.
  • 7
    • 33846219583 scopus 로고    scopus 로고
    • For Ni-catalyzed cross-coupling reactions, see:, and references therein
    • (b) For Ni-catalyzed cross-coupling reactions, see: Lee, C.-C.; Ke, W.-C.; Chan, K.-T.; Lai, C.-L.; Hu, C.-H.; Lee, H. M. Chem.-Eur. J. 2007, 13, 582 and references therein.
    • (2007) Chem.-Eur. J , vol.13 , pp. 582
    • Lee, C.-C.1    Ke, W.-C.2    Chan, K.-T.3    Lai, C.-L.4    Hu, C.-H.5    Lee, H.M.6
  • 8
    • 33846918696 scopus 로고    scopus 로고
    • For C-H activation reactions, see
    • (c) For C-H activation reactions, see: 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
  • 10
    • 0035753429 scopus 로고    scopus 로고
    • Bringmann, G.; Günther, C.; Ochse, M.; Schupp, O.; Tasler, S. Biaryls in Nature: A Multi-Faceted Class of Stereochemically, Biosynthetically, and Pharmacologically Intriguing Secondary Metabolites. In Progress in the Chemistry of Organic Natural Products; Herz, W., Falk, H., Kirby, G. W., Moore, R. E., Eds.; Springer-Verlag: New York, 2001; 82.
    • (b) Bringmann, G.; Günther, C.; Ochse, M.; Schupp, O.; Tasler, S. Biaryls in Nature: A Multi-Faceted Class of Stereochemically, Biosynthetically, and Pharmacologically Intriguing Secondary Metabolites. In Progress in the Chemistry of Organic Natural Products; Herz, W., Falk, H., Kirby, G. W., Moore, R. E., Eds.; Springer-Verlag: New York, 2001; Vol. 82.
  • 13
    • 0000718373 scopus 로고    scopus 로고
    • and references therein
    • (a) Pu, L. Chem. Rev. 1998, 98, 2405 and references therein.
    • (1998) Chem. Rev , vol.98 , pp. 2405
    • Pu, L.1
  • 27
    • 12344284768 scopus 로고    scopus 로고
    • Carboxylic acids and derivatives have also been used in Pd- or Rh-catalyzed couplings to replace the aryl halides. For an example in a Rh-catalyzed Suzuki-Miyaura-type reaction, see: (a) Goossen, L. J, Paetzold, J. Adv. Synth. Catal. 2004, 346, 1665. For examples in Pd-catalyzed Hecktype reactions, see
    • Carboxylic acids and derivatives have also been used in Pd- or Rh-catalyzed couplings to replace the aryl halides. For an example in a Rh-catalyzed Suzuki-Miyaura-type reaction, see: (a) Goossen, L. J.; Paetzold, J. Adv. Synth. Catal. 2004, 346, 1665. For examples in Pd-catalyzed Hecktype reactions, see:
  • 37
    • 34248377685 scopus 로고    scopus 로고
    • No starting material 1 or 2 was recovered. In addition to 3a, 1,3-dimethoxybenzene, anisole, and 4,4′-dimethoxybiphenyl were isolated.
    • No starting material 1 or 2 was recovered. In addition to 3a, 1,3-dimethoxybenzene, anisole, and 4,4′-dimethoxybiphenyl were isolated.
  • 38
    • 34248325149 scopus 로고    scopus 로고
    • 4, filtered, and concentrated under a vacuum. The residue was purified by flash chromatography on silica gel to afford pure biaryls after drying under a vacuum (0.1 mbar).
    • 4, filtered, and concentrated under a vacuum. The residue was purified by flash chromatography on silica gel to afford pure biaryls after drying under a vacuum (0.1 mbar).


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