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Volumn 128, Issue 28, 2006, Pages 9066-9073

Highly active Au(I) catalyst for the intramolecular exo- hydrofunctionalization of allenes with carbon, nitrogen, and oxygen nucleophiles

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CATALYSIS; CATALYSTS; GOLD; NITROGEN; THERMAL EFFECTS;

EID: 33746048429     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja062045r     Document Type: Article
Times cited : (428)

References (163)
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    • High activity in the Pd-catalyzed hydrofunctionalizalion is realized only in the cases of allenes activated by an aryl group or a heteroatom. (a) Kamijo, S.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 1747.
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  • 103
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    • For examples of the Pd(II)-catalyzed intermolecular hydrofunctionalization of allenes with carbon and heteroatom nucleophiles see: (a) Al-Masum, M.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 3809.
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    • note
    • 31,32 nucleophiles have appeared recently.
  • 143
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    • note
    • The presence of significant acid-catalyzed background reactions in the Aucatalyzed era-hydrofunctionalization of allenes was ruled out by the following control experiments: Treatment of 10 with a catalytic amount of HOTf (5 mol %) in dioxane at room temperature for 2 h led to no detectable formation of 11. Treatment of 14 with a catalytic amount of HOTs (10 mol %) in toluene at room temperature for 1 h led to no detectable formation of 15. Treatment of 21 with a catalytic amount of HOTf (10 mol %) in dioxane at room temperature for 2 h led to no detectable formation of 22.
  • 154
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    • note
    • 44h and subsequently converted to (S)-8 without further manipulation of the chiral allenyl moiety (See Supporting Information).
  • 156
    • 33746065826 scopus 로고    scopus 로고
    • note
    • Determination of the enantiomeric purity of (E)-18b and (Z)-18b was complicated by coelution of one enantiomer of (E)-18b with one enantiomer of (Z)-18b on HPLC (see Supporting Information).
  • 163
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    • note
    • 8a


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