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Volumn 25, Issue 19, 2006, Pages 4542-4553

Mechanisms of the transition metal-mediated hydroarylation of alkynes and allenes

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COMPLEXATION; FRIEDEL-CRAFTS REACTION; HYDROCARBONS; ORGANIC ACIDS; REACTION KINETICS; TRANSITION METAL COMPOUNDS;

EID: 33748787957     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0605332     Document Type: Article
Times cited : (135)

References (133)
  • 8
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    • Fürstner, A., Ed.; Springer-Verlag: Berlin
    • (b) Mori, M. Topics in Organometallic Chemistry; Fürstner, A., Ed.; Springer-Verlag: Berlin, 1998; Vol. 1, p 133-154.
    • (1998) Topics in Organometallic Chemistry , vol.1 , pp. 133-154
    • Mori, M.1
  • 23
    • 13844250379 scopus 로고    scopus 로고
    • (e) For a review on transition metal-catalyzed arylation of alkynes, see: Nevado, C.; Echavarren, A. M. Synthesis 2005, 167-182.
    • (2005) Synthesis , pp. 167-182
    • Nevado, C.1    Echavarren, A.M.2
  • 41
    • 33748760533 scopus 로고    scopus 로고
    • note
    • 2) has been proposed to be due to the higher electrophilicity (higher oxidation state of the metal center) and to the greater solubility of the catalyst in organic solvents.
  • 56
    • 0001996468 scopus 로고    scopus 로고
    • For reactions of alkynes, promoted by Lewis acids, with weak carbon nucleophiles, see: (a) Asao, N.; Matsukawa, Y.; Yamamoto, Y. Chem. Commun. 1996, 1513-1514.
    • (1996) Chem. Commun. , pp. 1513-1514
    • Asao, N.1    Matsukawa, Y.2    Yamamoto, Y.3
  • 64
    • 0000588488 scopus 로고    scopus 로고
    • For Ga as Lewis acid for promoting addition of carbon nucleophiles to alkynes, see: (a) Arisawa, M.; Akamatsu, K.; Yamaguchi, M. Org. Lett. 2001, 3, 789-790.
    • (2001) Org. Lett. , vol.3 , pp. 789-790
    • Arisawa, M.1    Akamatsu, K.2    Yamaguchi, M.3
  • 94
    • 8744259772 scopus 로고    scopus 로고
    • (a) For a review of gold-catalyzed reactions, see: Hashmi, A. S. K. Gold Bull. 2004, 37, 51-65.
    • (2004) Gold Bull. , vol.37 , pp. 51-65
    • Hashmi, A.S.K.1
  • 98
    • 33646440725 scopus 로고    scopus 로고
    • 3 as catalyst in organic synthesis: (a) Cook, G. R.; Hayashi R. Org. Lett. 2006, 8, 1045-1048.
    • (2006) Org. Lett. , vol.8 , pp. 1045-1048
    • Cook, G.R.1    Hayashi, R.2
  • 113
    • 33748802709 scopus 로고    scopus 로고
    • note
    • 2-C angle, which indeed should induce a lower steric hindrance with the methoxy substituent.
  • 115
    • 33748802961 scopus 로고    scopus 로고
    • note
    • 1 = 0.611).
  • 118
    • 33748777034 scopus 로고    scopus 로고
    • note
    • The energy minimization of the supposed In(III)-carbenic intermediate of type 8a directly led to the formation of the 9-halo-phenanthrene framework (analogue to 9).
  • 119
  • 121


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