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Volumn 69, Issue 20, 2004, Pages 6942-6944

Palladium-catalyzed dehydroarylation of triarylmethanols and their coupling with unsaturated compounds accompanied by C-C bond cleavage

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; CHEMICAL BONDS; KETONES; PALLADIUM; REACTION KINETICS; UNSATURATED COMPOUNDS;

EID: 4644302718     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049031t     Document Type: Article
Times cited : (78)

References (32)
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    • note
    • 6a The cyclization process is considered to be reversible under the present conditions.
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    • A reviewer has kindly suggested a possibility that intermediate B reversibly reacts with the ketone moiety liberated to regenerate A. Such a nucleophilic arylation of ketones with ArPd(II) species is known to occur intramolecularly: (a) Quan, L. G.; Lamrani, M.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 4827. (b) Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardía, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587. Thus, the selective formation of 13 as well as 12 under the present conditions (Table 2) could be attributed to the reversibility.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 4827
    • Quan, L.G.1    Lamrani, M.2    Yamamoto, Y.3
  • 25
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    • A reviewer has kindly suggested a possibility that intermediate B reversibly reacts with the ketone moiety liberated to regenerate A. Such a nucleophilic arylation of ketones with ArPd(II) species is known to occur intramolecularly: (a) Quan, L. G.; Lamrani, M.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 4827. (b) Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardía, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587. Thus, the selective formation of 13 as well as 12 under the present conditions (Table 2) could be attributed to the reversibility.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 1587
    • Solé, D.1    Vallverdú, L.2    Solans, X.3    Font-Bardía, M.4    Bonjoch, J.5
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    • ArB: (a) Cho, C. S.; Motofusa, S.; Ohe, K.; Uemura, S.; Shim, S. C. J. Org. Chem. 1995, 60, 883. (b) Oh, C. H.; Jung, H. H.; Kim, K. S.; Kim, N. Angew. Chem., Int. Ed. 2003, 42, 805. (c) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Angew. Chem., Int. Ed. 2003, 42, 2768.
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    • ArB: (a) Cho, C. S.; Motofusa, S.; Ohe, K.; Uemura, S.; Shim, S. C. J. Org. Chem. 1995, 60, 883. (b) Oh, C. H.; Jung, H. H.; Kim, K. S.; Kim, N. Angew. Chem., Int. Ed. 2003, 42, 805. (c) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Angew. Chem., Int. Ed. 2003, 42, 2768.
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    • Oh, C.H.1    Jung, H.H.2    Kim, K.S.3    Kim, N.4
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    • ArB: (a) Cho, C. S.; Motofusa, S.; Ohe, K.; Uemura, S.; Shim, S. C. J. Org. Chem. 1995, 60, 883. (b) Oh, C. H.; Jung, H. H.; Kim, K. S.; Kim, N. Angew. Chem., Int. Ed. 2003, 42, 805. (c) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Angew. Chem., Int. Ed. 2003, 42, 2768.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 2768
    • Nishikata, T.1    Yamamoto, Y.2    Miyaura, N.3


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