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For the zinc(II), triethylamine and 2-dimethylaminoethanol-promoted reaction of terminal acetylene with nitrones, see: R. Fässler, D. E. Frantz, J. Oetiker, E. M. Carreira, Angew. Chem., Int. Ed. 2002, 41, 3054.
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For the zinc(II), triethylamine and 2-dimethylaminoethanol-promoted reaction of terminal acetylene with nitrones, see: R. Fässler, D. E. Frantz, J. Oetiker, E. M. Carreira, Angew. Chem., Int. Ed. 2002, 41, 3054.
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For the dialkylzinc-assisted alkynylation of nitrones, see
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For the dialkylzinc-assisted alkynylation of nitrones, see: S. Pinet, S. U. Pandya, P. Y. Chavant, A. Ayling, Y. Vallee, Org. Lett. 2002, 4, 1463.
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0037099190
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For the transition metalcatalyzed enantioselective synthesis of propargylamines, see: d
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For the transition metalcatalyzed enantioselective synthesis of propargylamines, see: d) C. Koradin, K. Polborn, P. Knochel, Angew. Chem., Int. Ed. 2002, 41, 2535.
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d) Y. Kuninobu, Y. Nishina, C. Nakagawa, K. Takai, J. Am. Chem. Soc. 2006, 128, 12376.
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e) Y. Kuninobu, A. Kawata, K. Takai, Org. Lett. 2005, 7, 4823.
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f) Y. Kuninobu, A. Kawata, K. Takai, J. Am. Chem. Soc. 2006, 128, 11368.
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23
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33847620813
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1H NMR yields were determined by using 1,1,2,2-tetrachloroethane as an internal standard.
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1H NMR yields were determined by using 1,1,2,2-tetrachloroethane as an internal standard.
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24
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33847623797
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A ketimine, which was derived from the reaction between acetophenone and aniline, did not give the corresponding propargylamine even at 80°C.
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A ketimine, which was derived from the reaction between acetophenone and aniline, did not give the corresponding propargylamine even at 80°C.
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25
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0001845650
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For reports that those triflates act as a Lewis acid and activate aldimines, see
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For reports that those triflates act as a Lewis acid and activate aldimines, see: S. Kobayashi, Top. Organomet. Chem. 1999, 2, 63.
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Kobayashi, S.1
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26
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33847681905
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2. The result indicates that aldimines or propargyl amines did not increase the nucleophilicity of trimethylsilylacetylene (2a) by deprotonation.
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2. The result indicates that aldimines or propargyl amines did not increase the nucleophilicity of trimethylsilylacetylene (2a) by deprotonation.
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27
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0001540726
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For examples of hydride-alkynyl-rhenium complexes, see: a K.-W. Lee, W. T. Pennington, A. W. Cordes, T. L. Brown, J. Am. Chem. Soc. 1985, 107, 631
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For examples of hydride-alkynyl-rhenium complexes, see: a) K.-W. Lee, W. T. Pennington, A. W. Cordes, T. L. Brown, J. Am. Chem. Soc. 1985, 107, 631.
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29
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33847685327
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Although the reaction proceeded with only 5.0 mol, of copper(I) chloride, the yield of propargylamine (4) was low 62
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Although the reaction proceeded with only 5.0 mol % of copper(I) chloride, the yield of propargylamine (4) was low (62%).
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