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Volumn 41, Issue 2, 2012, Pages 130-134

Transition-metal-free coupling reactions of aryl halides

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EID: 84856539505     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2012.130     Document Type: Review
Times cited : (115)

References (31)
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    • For a review on transition-metal catalysis from a mechanistic view, see, University Science Book, Sausalito
    • For a review on transition-metal catalysis from a mechanistic view, see: J. F. Hartwig, Organotransition Metal Chemistry: From Bonding to Catalysis, University Science Book, Sausalito, 2010.
    • (2010) Organotransition Metal Chemistry: From Bonding to Catalysis
    • Hartwig, J.F.1
  • 4
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    • For reviews, see
    • For reviews, see: a) J.-M. Savéant, Tetrahedron 1994, 50, 10117.
    • (1994) Tetrahedron , vol.50 , pp. 10117
    • Savéant, J.-M.1
  • 6
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    • RN1 reaction
    • RN1 reaction, see: a) J. F. Bunnett, Acc. Chem. Res. 1978, 11, 413.
    • (1978) Acc. Chem. Res. , vol.11 , pp. 413
    • Bunnett, J.F.1
  • 8
    • 0001190580 scopus 로고
    • RN1 reaction with aryl halides. For examples, see:
    • RN1 reaction with aryl halides. For examples, see: a) R. A. Rossi, J. F. Bunnett, J. Org. Chem. 1973, 38, 3020.
    • (1973) J. Org. Chem. , vol.38 , pp. 3020
    • Rossi, R.A.1    Bunnett, J.F.2
  • 13
    • 0000179388 scopus 로고
    • The reaction of Grignard reagents (R-MgX) with certain alkyl halides (R'-X: R' = tert-alkyl, allyl) giving R-R' is thought to proceed through SET from R-MgX to R'-X followed by coupling between the resulting radicals R and R', For examples, see:
    • The reaction of Grignard reagents (R-MgX) with certain alkyl halides (R'-X: R' = tert-alkyl, allyl) giving R-R' is thought to proceed through SET from R-MgX to R'-X followed by coupling between the resulting radicals R and R'. For examples, see: a) M. Ohno, K. Shimizu, K. Ishizaki, T. Sasaki, S. Eguchi, J. Org. Chem. 1988, 53, 729.
    • (1988) J. Org. Chem. , vol.53 , pp. 729
    • Ohno, M.1    Shimizu, K.2    Ishizaki, K.3    Sasaki, T.4    Eguchi, S.5
  • 15
    • 76149113261 scopus 로고    scopus 로고
    • An unpublished result. For iron-catalyzed coupling of aryl halides with arenes, see
    • An unpublished result. For iron-catalyzed coupling of aryl halides with arenes, see: a) F. Vallée, J. J. Mousseau, A. B. Charette, J. Am. Chem. Soc. 2010, 132, 1514.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 1514
    • Vallée, F.1    Mousseau, J.J.2    Charette, A.B.3
  • 18
    • 58449085051 scopus 로고    scopus 로고
    • Tert-Butoxide-mediated arylation of arenes has a precedent but is applicable only to electron-deficient nitrogen heterocycles such as pyrazine, where involvement of aryl radicals derived from aryl iodides is mentioned
    • tert-Butoxide-mediated arylation of arenes has a precedent but is applicable only to electron-deficient nitrogen heterocycles such as pyrazine, where involvement of aryl radicals derived from aryl iodides is mentioned. S. Yanagisawa, K. Ueda, T. Taniguchi, K. Itami, Org. Lett. 2008, 10, 4673.
    • (2008) Org. Lett. , vol.10 , pp. 4673
    • Yanagisawa, S.1    Ueda, K.2    Taniguchi, T.3    Itami, K.4
  • 19
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    • Internal temperature measured by a thermometer, the bulb of which was placed at the middle of a benzene solvent in a flask heated with an oil bath (bath temperature = 185 °C)
    • Internal temperature measured by a thermometer, the bulb of which was placed at the middle of a benzene solvent in a flask heated with an oil bath (bath temperature = 185 °C).
  • 20
    • 79956102547 scopus 로고    scopus 로고
    • In the original report (ref. 9), we proposed a different mechanism, where steps a, b, and d are the same. Deeper understanding on the related chemistry after investigation of the coupling reactions with alkenes and aryl Grignard reagents as well as a stimulating interpretation by Studer and Curran on our and others' reports prompt us to take the present mechanism. For the report by Studer and Curran, see
    • In the original report (ref. 9), we proposed a different mechanism, where steps a, b, and d are the same. Deeper understanding on the related chemistry after investigation of the coupling reactions with alkenes and aryl Grignard reagents as well as a stimulating interpretation by Studer and Curran on our and others' reports prompt us to take the present mechanism. For the report by Studer and Curran, see: A. Studer, D. P. Curran, Angew. Chem., Int. Ed. 2011, 50, 5018.
    • (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 5018
    • Studer, A.1    Curran, D.P.2
  • 22
    • 84856525769 scopus 로고    scopus 로고
    • By-production of some polymeric compounds lowered the yield. Reduction of aryl halides is another major side reaction in the MizorokiHeck type reaction
    • By-production of some polymeric compounds lowered the yield. Reduction of aryl halides is another major side reaction in the MizorokiHeck type reaction.


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