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Volumn 75, Issue 5, 2010, Pages 1791-1794

Cu-catalyzed arylation of phenols: Synthesis of sterically hindered and heteroaryl diaryl ethers

Author keywords

[No Author keywords available]

Indexed keywords

ARYL IODIDES; ARYLATIONS; CHEMICAL EQUATIONS; DIARYL ETHERS; PICOLINIC ACID;

EID: 77949297216     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo9026935     Document Type: Article
Times cited : (180)

References (56)
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    • Chan, D. M. T.; Monaco, K. L.; Wang, R. P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933-2936.
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    • Harkal, S.; Kumar, K.; Michalik, D.; Zapf, A.; Jackstell, R.; Rataboul, F.; Riermeier, T.; Monsees, A.; Beller, M. tetrahedron Lett. 2005, 46, 3237-3240.
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    • Takeuchi, D.; Asano, I.; Osakada, K. J. Org. Chem. 2006, 71, 86148617.
  • 48
    • 77949310456 scopus 로고    scopus 로고
    • For a full list of copper-catalyzed diaryl ether formation, see the Supporting Information
    • For a full list of copper-catalyzed diaryl ether formation, see the Supporting Information.
  • 50
    • 77949310627 scopus 로고    scopus 로고
    • Current prices from Sigma-Aldrich: picolinic acid $26.4/mol, pyrrole2-carboxylic acid $2346/mol, and. N,N-dimethylglycine $996/mol.
    • Current prices from Sigma-Aldrich: picolinic acid $26.4/mol, pyrrole2-carboxylic acid $2346/mol, and. N,N-dimethylglycine $996/mol.
  • 53
    • 77949293504 scopus 로고    scopus 로고
    • The control experiments without catalyst were performed to confirm these products are not generated by SNAr- reaction, but by picolinic acidligated copper-catalyzed C-O bond forming reaction
    • NAr- reaction, but by picolinic acidligated copper-catalyzed C-O bond forming reaction.
  • 54
    • 77949288845 scopus 로고    scopus 로고
    • We found that the reduction of aryl halide (Ar-X to Ar-H) was obtained as the major side reaction. Thus in Table 2, ethylbenzoate (5%, entry 2) and benzaldehyde (2%, entry 3) were detected. Similarly, isoquinoline (10%, entry 7; 5%, entry 8), benzo[b]thiophene-2-carbaldehyde (entry 1), and pyridine (1%, entry 4) were detected in Table 3 as were quinoline (2%, entry 3) and a trace of nicotinonitrile in Table 4, entry 5.
    • We found that the reduction of aryl halide (Ar-X to Ar-H) was obtained as the major side reaction. Thus in Table 2, ethylbenzoate (5%, entry 2) and benzaldehyde (2%, entry 3) were detected. Similarly, isoquinoline (10%, entry 7; 5%, entry 8), benzo[b]thiophene-2-carbaldehyde (entry 1), and pyridine (1%, entry 4) were detected in Table 3 as were quinoline (2%, entry 3) and a trace of nicotinonitrile in Table 4, entry 5.


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