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Volumn 64, Issue 26, 2008, Pages 6073-6081

Direct coupling of arenes and iodoarenes catalyzed by a rhodium complex with a strongly π-accepting phosphite ligand

Author keywords

[No Author keywords available]

Indexed keywords

ALKOXYBENZENE DERIVATIVE; CARBON; FURAN DERIVATIVE; HETEROARENE DERIVATIVE; HYDROGEN; INDOLE DERIVATIVE; IODOARENE DERIVATIVE; PHOSPHITE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRROLE DERIVATIVE; RHODIUM; THIOPHENE DERIVATIVE;

EID: 43849100263     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.053     Document Type: Article
Times cited : (74)

References (89)
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    • Pd-catalyzed direct C-H arylation of six-membered heteroarenes:
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    • Pd-catalyzed direct C-H arylation of benzene derivatives:
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    • Rh-catalyzed direct arylation of aromatic C-H bonds:
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    • Ru-catalyzed direct arylation of aromatic C-H bonds:
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    • (2004) Chem. Commun. , pp. 1926
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    • For examples of such a π-donation effect of halides to transition metals, see:
    • For examples of such a π-donation effect of halides to transition metals, see:
  • 78
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    • 2 are 2.3561(8) Å, 2.404(4) Å, and 2.371(2) Å, respectively. For references, see:
    • 2 are 2.3561(8) Å, 2.404(4) Å, and 2.371(2) Å, respectively. For references, see:
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    • note
    • The addition of DME suppressed the formation of diarylated product. However, the role is DME has not been completely understood.
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    • note
    • Sames also proposed a mechanism based on electrophilic metalation in his Rh-catalyzed direct arylation of indoles and pyrroles (See Ref. 8e).
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    • A study on the mechanism of the present rhodium catalysis by density functional theory (DFT) calculation will be reported in due course. Coutelier, O.; Shiota, Y.; Yanagisawa, S.; Inoue, T.; Noyori, R.; Yoshizawa, K.; Itami, K., in preparation.
    • A study on the mechanism of the present rhodium catalysis by density functional theory (DFT) calculation will be reported in due course. Coutelier, O.; Shiota, Y.; Yanagisawa, S.; Inoue, T.; Noyori, R.; Yoshizawa, K.; Itami, K., in preparation.
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    • note
    • The yield of arylation products (6 and 7) gradually decreased by decreasing the amount of anisole (5) employed: 51% (3f/5=1:27), 48% (3f/5=1:10), 42% (3f/5/n-octane=1:5:6; n-octane was added as co-solvent), 25% (3f/5/n-octane=1:2:6; n-octane was added as co-solvent).


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