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Volumn 79, Issue 2, 2014, Pages 818-822

Copper-catalyzed allylation of a,a-difluoro-substituted organozinc reagents

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLATION; CATALYSIS; ORGANOMETALLICS; SUBSTITUTION REACTIONS;

EID: 84896694160     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4024705     Document Type: Article
Times cited : (55)

References (30)
  • 3
    • 0029895833 scopus 로고    scopus 로고
    • For a general overview
    • (a) For a general overview, see: Tozer, M. J.; Herpin, T. F. Tetrahedron 1996, 52, 8619-8683.
    • (1996) Tetrahedron , Issue.52 , pp. 8619-8683
    • Tozer, M.1    Herpin, T.2
  • 4
    • 0038640102 scopus 로고    scopus 로고
    • Difluorocyclopropanes Constitute A Specific Class And Can Be Accessed By Difluorocarbene Addition Reactions
    • Difluorocyclopropanes constitute a specific class and can be accessed by difluorocarbene addition reactions. See: Dolbier, W. R.; Battiste, M. A. Chem. Rev. 2003, 103, 1071-1098.
    • (2003) Chem. Rev. , Issue.103 , pp. 1071-1098
    • Dolbier, W.R.1    Battiste, M.A.2
  • 10
    • 84863633032 scopus 로고    scopus 로고
    • A stepwise assembly of C-CF2-C units from Me3SiCN, CF2, and aldehydes/imines, which requires isolation of the intermediate Me3SiCF2CN, has been described
    • A stepwise assembly of C-CF2-C units from Me3SiCN, CF2, and aldehydes/imines, which requires isolation of the intermediate Me3SiCF2CN, has been described. See: Kosobokov, M. D.; Dilman, A. D.; Levin, V. V.; Struchkova, M. I. J. Org. Chem. 2012, 77, 5850-5855.
    • (2012) J. Org. Chem. , Issue.77 , pp. 5850-5855
    • Kosobokov, M.1    Dilman, A.2    Levin, V.3    Struchkova, M.4
  • 12
  • 15
    • 84867216409 scopus 로고    scopus 로고
    • For reactions of trifluoromethylcopper species with allyl or propargyl electrophiles, see:
    • For reactions of trifluoromethylcopper species with allyl or propargyl electrophiles, see: (a) Miyake, Y.; Ota, S.; Nishibayashi, Y. Chem. Eur. J. 2012, 18, 13255-13258.
    • (2012) Chem. Eur. J. , vol.18 , pp. 13255-13258
    • Miyake, Y.1    Ota, S.2    Nishibayashi, Y.3
  • 20
    • 33845376895 scopus 로고
    • For a palladium-catalyzed reaction of perfluoroalkyl iodides, zinc, and allyl bromides
    • For a palladium-catalyzed reaction of perfluoroalkyl iodides, zinc, and allyl bromides, see: Kitazume, T.; Ishikawa, N. J. Am. Chem. Soc. 1985, 107, 5186-5191.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 5186-5191
    • Kitazume, T.1    Ishikawa, N.2
  • 22
    • 84887510998 scopus 로고    scopus 로고
    • Li, L.; Wang, F.; Ni, C.; Hu, J.
    • Li, L.; Wang, F.; Ni, C.; Hu, J. Angew. Chem., Int. Ed. 2013, 52, 12390-12394.
    • (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 12390-12394
  • 24
    • 0007573019 scopus 로고
    • The reaction of allyl chlorides with π-nucleophiles promoted by ZnCl2 has been described
    • The reaction of allyl chlorides with π-nucleophiles promoted by ZnCl2 has been described. See: Reetz, M. T.; Hubner, F.; Huttenhain, S. H.; Heimbach, H.; Schwellnus, K.; Walz, P. Chem. Ber. 1984, 117, 322-335.
    • (1984) Chem. Ber. , Issue.117 , pp. 322-335
    • Reetz, M.1    Hubner, F.2    Huttenhain, S.3    Heimbach, H.4    Schwellnus, K.5    Walz, P.6
  • 25
    • 84896752592 scopus 로고    scopus 로고
    • Attempts to observe intermediate 5 were unsuccessful. Mixing of reagent 2a with stoichiometric amounts of phen and CuI at -25 °C gave a precipitate, while subsequent recording of the 19F NMR spectrum at room temperature gave no signals
    • Attempts to observe intermediate 5 were unsuccessful. Mixing of reagent 2a with stoichiometric amounts of phen and CuI at -25 °C gave a precipitate, while subsequent recording of the 19F NMR spectrum at room temperature gave no signals.
  • 26
    • 84896756239 scopus 로고    scopus 로고
    • For a similar erosion of the double-bond configuration along with α-attack in reaction of trifluoromethylcopper species, see ref 10a
    • For a similar erosion of the double-bond configuration along with α-attack in reaction of trifluoromethylcopper species, see ref 10a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.