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Volumn 72, Issue 3, 2007, Pages 923-929

Synthetic and mechanistic studies of indium-mediated allylation of imines in ionic liquids

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; BROMINE COMPOUNDS; INDIUM; IONIC CONDUCTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL);

EID: 33846906499     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062198x     Document Type: Article
Times cited : (52)

References (51)
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    • For, review, see
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  • 9
    • 0038106171 scopus 로고    scopus 로고
    • For reviews of metal-mediated allylation of imines in organic solvents, see: a
    • For reviews of metal-mediated allylation of imines in organic solvents, see: (a) Bloch, R. Chem. Rev. 1998, 98, 1407.
    • (1998) Chem. Rev , vol.98 , pp. 1407
    • Bloch, R.1
  • 19
    • 33846935115 scopus 로고    scopus 로고
    • Paquette, L. A. In Green Chemistry, Frontiers in Chemically Benign Synthesis and Processes; Anastas, P. J., Williamson, T. C., Eds.; Oxford University Press: Oxford, U.K., New York, NY, 1998: p 261 and footnote 49.
    • (a) Paquette, L. A. In Green Chemistry, Frontiers in Chemically Benign Synthesis and Processes; Anastas, P. J., Williamson, T. C., Eds.; Oxford University Press: Oxford, U.K., New York, NY, 1998: p 261 and footnote 49.
  • 37
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    • A likely drawback associated with solvent-free reaction is that many solid aldehydes did not give a satisfactory result as the mixture tended to solidify readily and gave incomplete reaction
    • Andrews, P. C.; Peatt, A. C.; Raston, C. L. Tetrahedron Lett. 2004, 45, 243. A likely drawback associated with solvent-free reaction is that many solid aldehydes did not give a satisfactory result as the mixture tended to solidify readily and gave incomplete reaction.
    • (2004) Tetrahedron Lett , vol.45 , pp. 243
    • Andrews, P.C.1    Peatt, A.C.2    Raston, C.L.3
  • 38
    • 1342311424 scopus 로고    scopus 로고
    • At present, this method is applicable only to sulfonimines and aldimines derived from aromatic anilines and aldehydes
    • Andrews, P. C.; Peatt, A. C.; Raston, C. L. Green Chem. 2004, 6, 119. At present, this method is applicable only to sulfonimines and aldimines derived from aromatic anilines and aldehydes.
    • (2004) Green Chem , vol.6 , pp. 119
    • Andrews, P.C.1    Peatt, A.C.2    Raston, C.L.3
  • 46
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    • 8. Araki, S.; Ito, H.; Katsumura, N.; Butsugan, Y. J. Organomet. Chem. 1989, 369, 291.
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    • The formation of allenylindium(I) and allenlylindium(III) dibromide in the reaction of indium with propargyl bromide has been reported. Miao, W.; Chung, L. W.; Wu, Y.-D.; Chan, T. H. J. Am. Chem. Soc. 2004, 126, 13326.
    • The formation of allenylindium(I) and allenlylindium(III) dibromide in the reaction of indium with propargyl bromide has been reported. Miao, W.; Chung, L. W.; Wu, Y.-D.; Chan, T. H. J. Am. Chem. Soc. 2004, 126, 13326.
  • 48
    • 0000753976 scopus 로고
    • Iminium Salts in Organic Chemistry
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    • Bohme, H.1    Viehe, H.G.2
  • 49
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    • This is in contrast to the reaction of organolithiums, where both 1,2- and 1,4-addition were observed. See, for examples: Tamioka, K, Inoue, I, Shindo, M, Kago, K. Tetrahedron Lett. 1990, 31, 6681
    • This is in contrast to the reaction of organolithiums, where both 1,2- and 1,4-addition were observed. See, for examples: Tamioka, K.; Inoue, I.; Shindo, M.; Kago, K. Tetrahedron Lett. 1990, 31, 6681.
  • 50
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    • 3 carbon linked to nitrogen, the corresponding aldimines are generally less reactive, leading to poor yields and incomplete reactions or even no reaction at all. For examples, see: (a) Beuchet, P.; Marrec, N. L.; Mosset, P. Tetrahedron Lett. 1992, 33, 5959.
    • 3 carbon linked to nitrogen, the corresponding aldimines are generally less reactive, leading to poor yields and incomplete reactions or even no reaction at all. For examples, see: (a) Beuchet, P.; Marrec, N. L.; Mosset, P. Tetrahedron Lett. 1992, 33, 5959.


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