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Volumn 69, Issue 11, 2004, Pages 3943-3949

Selective iron-catalyzed cross-coupling reactions of Grignard reagents with enol triflates, acid chlorides, and dichloroarenes

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CATALYSIS; CHEMICAL BONDS; CHLORINE COMPOUNDS; ENVIRONMENTAL IMPACT; IRON; SALTS;

EID: 2442656574     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0498866     Document Type: Article
Times cited : (302)

References (94)
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    • (a) Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998.
    • (1998) Metal-catalyzed Cross-coupling Reactions
  • 2
    • 0003535745 scopus 로고    scopus 로고
    • Miyaura, N., Ed.; Top. Curr. Chem.; Springer: Berlin
    • (b) Cross-Coupling Reactions. A Practical Guide; Miyaura, N., Ed.; Top. Curr. Chem.; Springer: Berlin, 2002; Vol. 219.
    • (2002) Cross-Coupling Reactions. A Practical Guide , vol.219
  • 3
    • 0000891348 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • (c) Knight, D. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3; p 481.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 481
    • Knight, D.W.1
  • 13
    • 0035128727 scopus 로고    scopus 로고
    • For selected contributions from this laboratory, see: (a) Fürstner, A.; Leitner, A. Synlett. 2001, 290.
    • (2001) Synlett , pp. 290
    • Fürstner, A.1    Leitner, A.2
  • 70
    • 0027180141 scopus 로고
    • For a review of enol triflate chemistry including various types of cross-coupling reactions, see: Ritter, K. Synthesis 1993, 735.
    • (1993) Synthesis , pp. 735
    • Ritter, K.1
  • 71
    • 0037163310 scopus 로고    scopus 로고
    • See the following for leading references on metal-catalyzed cross-coupling reactions of enol triflates with Grignard reagents and literature cited therein: (a) Miller, J. A. Tetrahedron Lett. 2002, 43, 7111.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 7111
    • Miller, J.A.1
  • 73
    • 0343922815 scopus 로고
    • Jpn. Kokai Tokkyo Koho JP07,196,491, 1995
    • Oomura, Y.; Shiraishi, T.; Takeoka, J. Jpn. Kokai Tokkyo Koho JP07,196,491, 1995; Chem. Abstr. 1995, 123, 246850.
    • (1995) Chem. Abstr. , vol.123 , pp. 246850
    • Oomura, Y.1    Shiraishi, T.2    Takeoka, J.3
  • 74
    • 85039539865 scopus 로고    scopus 로고
    • note
    • Iron-catalyzed reactions of arylmagnesium halides in general are known to be more problematic because the catalytic homodimerization of the Grignard reagent can seriously compete with or even outperform effective cross coupling, cf. refs 7 and 21. In line with this, varying amounts of biphenyl or substituted biphenyls accompany the cross-coupling products shown in Table 1, which, however, are generally readily purified by flash chromatography.
  • 78
    • 85039537466 scopus 로고    scopus 로고
    • note
    • Note that alkyllithium reagents in general were previously shown to be unsuitable for iron-catalyzed cross-coupling reactions, cf. ref 7.
  • 79
    • 85039534148 scopus 로고    scopus 로고
    • note
    • In this context, it is noteworthy that iron-catalyzed cross-couplings of MeMgX with aryl chlorides and triflates seem to be confined to special cases, cf. ref 9b.
  • 80
    • 0000608756 scopus 로고
    • For alkylations of alkenyl halides with stoichiometric amounts of organoiron reagents of different formal compositions formed in situ, see: (a) Corey, E. J.; Posner, G. H. Tetrahedron Lett. 1970, 11, 315.
    • (1970) Tetrahedron Lett. , vol.11 , pp. 315
    • Corey, E.J.1    Posner, G.H.2
  • 86
    • 0033118177 scopus 로고    scopus 로고
    • For a general review on the acylation of organometallic reagents, see: Dieter, R. K. Tetrahedron 1999, 55, 4177.
    • (1999) Tetrahedron , vol.55 , pp. 4177
    • Dieter, R.K.1
  • 87
    • 85039531003 scopus 로고    scopus 로고
    • note
    • Note that the loss of enantiomeric purity in the conversion of the cysteine derived acid chloride to the corresponding methyl ketone depicted in entry 28 is not caused by the iron-catalyzed cross-coupling but reflects the inherent configurational lability of amino acid chlorides; compare also footnote c in Table 2.
  • 91
    • 0001659917 scopus 로고
    • For related palladium-catalyzed monoalkylation reactions of dibromobenzene, chlorobromobenzene, or chlorofluorobenzene, see: (a) Sekiya, A. ; Ishikawa, N. J. Organomet. Chem. 1977, 125, 281.
    • (1977) J. Organomet. Chem. , vol.125 , pp. 281
    • Sekiya, A.1    Ishikawa, N.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.