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Volumn 3, Issue 10, 2011, Pages 1567-1571

Iron-catalyzed isomerizations of olefins

Author keywords

Cross coupling; Domino reactions; Grignard reactions; Iron; Isomerization; Styrenes

Indexed keywords


EID: 80053616750     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201100207     Document Type: Article
Times cited : (99)

References (59)
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    • For example the Shell higher olefin, Takasago menthole, BASF vitaminA, DuPont hydrocyanation processes. For reviews of academic and technical olefin isomerization processes, see:
    • For example the Shell higher olefin, Takasago menthole, BASF vitaminA, DuPont hydrocyanation processes. For reviews of academic and technical olefin isomerization processes, see:
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    • Selected examples: Friedel-Crafts-type reactions:
    • Selected examples: Friedel-Crafts-type reactions:
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    • W. R. Roush in Comprehensive Organic Synthesis (Eds.: B.M. Trost, I. Fleming, C.H. Heathcock), Pergamon, Oxford, 1991, Vol.2, p.1;
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    • Selected recent examples:
    • Selected recent examples:
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    • 2 flash chromatography (cyclohexane/ethyl acetate);
    • 2 flash chromatography (cyclohexane/ethyl acetate);
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    • For more details, see Supporting Information;
    • For more details, see Supporting Information;
  • 39
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    • p-Anisylpenta-2,4-diene was prepared from pentadienyl acetate according to Ref.[8].
    • p-Anisylpenta-2, 4-diene was prepared from pentadienyl acetate according to Ref.[8].
  • 40
    • 69949165772 scopus 로고    scopus 로고
    • The oxidative biaryl formation is hindered in cases where ortho-substituted aryl moieties are present. For the generation of iron(II) catalysts in the presence of bulky arylmagnesium halides, see
    • The oxidative biaryl formation is hindered in cases where ortho-substituted aryl moieties are present. For the generation of iron(II) catalysts in the presence of bulky arylmagnesium halides, see: D. Noda, Y. Sunada, T. Hatakeyama, M. Nakamura, H. Nagashima, J. Am. Chem. Soc. 2009, 131, 6078-6079.
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    • 2]-allylbenzene from methyl phenylpropiolate, see
    • 2]-allylbenzene from methyl phenylpropiolate, see: W. T. Hendrix, J. L. vonRosenberg, J. Am. Chem. Soc. 1976, 98, 4850-4852.
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    • Similar mechanistic scenarios have been reported;
    • Similar mechanistic scenarios have been reported;
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    • Phosphine-ruthenium(0) catalysts, C-C.
    • Phosphine-ruthenium(0) catalysts: E. O. Sherman, Jr., M. Olson, J. Organomet. Chem. 1979, 172, C13-C19.
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    • For hydridoiron complexes in catalysis, see
    • For hydridoiron complexes in catalysis, see: H. Nakazawa, M. Itazaki, Top. Organomet. Chem. 2011, 33, 27-81;
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    • Reactions with a formal iron hydride generated upon β-hydride elimination of alkyliron intermediates
    • Reactions with a formal iron hydride generated upon β-hydride elimination of alkyliron intermediates: W. M. Czaplik, S. Grupe, M. Mayer, A. JacobivonWangelin, Chem. Commun. 2010, 46, 6350-6352.
    • (2010) Chem. Commun. , vol.46 , pp. 6350-6352
    • Czaplik, W.M.1    Grupe, S.2    Mayer, M.3    JacobivonWangelin, A.4
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    • Average of five runs at large scales (5mmol reactions). After an induction period of 15min required for the (reductive)catalyst formation, no further biaryl formation was observed during the reaction under strictly anaerobic conditions. Similar observations pointing to an iron(0) catalyst in the presence of aryl Grignard species have been reported
    • Average of five runs at large scales (5mmol reactions). After an induction period of 15min required for the (reductive)catalyst formation, no further biaryl formation was observed during the reaction under strictly anaerobic conditions. Similar observations pointing to an iron(0) catalyst in the presence of aryl Grignard species have been reported: G. Cahiez, V. Habiak, C. Duplais, A. Moyeux, Angew. Chem. 2007, 119, 4442-4444; Angew. Chem. Int. Ed. 2007, 46, 4364-4366;
    • (2007) Angew. Chem. 2007, 119, 4442-4444; Angew. Chem. Int. Ed. , vol.46 , pp. 4364-4366
    • Cahiez, G.1    Habiak, V.2    Duplais, C.3    Moyeux, A.4
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    • EXAFS and XANES spectroscopy have been used for the detection of iron(0) species under such conditions: A. Welther, M. Bauer, A. JacobivonWangelin, unpublished results.
    • EXAFS and XANES spectroscopy have been used for the detection of iron(0) species under such conditions: A. Welther, M. Bauer, A. JacobivonWangelin, unpublished results.
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    • For alternative mechanistic postulates of iron-catalyzed cross-coupling reactions, see also:
    • A. Fürstner, R. Martin, H. Krause, G. Seidel, R. Goddard, C. W. Lehmann, J. Am. Chem. Soc. 2008, 130, 8773-8787. For alternative mechanistic postulates of iron-catalyzed cross-coupling reactions, see also:
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 8773-8787
    • Fürstner, A.1    Martin, R.2    Krause, H.3    Seidel, G.4    Goddard, R.5    Lehmann, C.W.6
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    • ref.[10];
    • ref.[10];
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    • For the direct synthesis of substituted styrenes via iron-catalyzed cross-coupling, see, and references therein.
    • For the direct synthesis of substituted styrenes via iron-catalyzed cross-coupling, see: W. M. Czaplik, M. Mayer, A. Jacobi von Wangelin, ChemCatChem 2011, 3, 135-138, and references therein.
    • (2011) ChemCatChem , vol.3 , pp. 135-138
    • Czaplik, W.M.1    Mayer, M.2    Wangelin, A.J.V.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.