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76149114419
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See the Supporting Information for details
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See the Supporting Information for details.
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31
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0037149057
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N-Aryltetrahydroisoquinolines were prepared via Buchwald - Hartwig coupling (see: Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581).
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N-Aryltetrahydroisoquinolines were prepared via Buchwald - Hartwig coupling (see: Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581).
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32
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For an alternative approach to N-arylation, see
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For an alternative approach to N-arylation, see: Barker, T. J.; Jarvo, E. R. J. Am. Chem. Soc. 2009, 131, 15598.
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Jarvo, E.R.2
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33
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0000474999
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An insightful reviewer suggested that this reaction may be mediated by singlet O2 sensitization by 4 see: Demas, J. N, Harris, E. W, McBride, R. P. J. Am. Chem. Soc. 1977, 99, 3547
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2 sensitization by 4 (see: Demas, J. N.; Harris, E. W.; McBride, R. P. J. Am. Chem. Soc. 1977, 99, 3547).
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2-mediated oxidation of dibenzylamine to the corresponding imine (see: Jiang, G.; Chen, J.; Huang, J.-S.; Che, C.-M. Org. Lett. 2009, 11, 4568):
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2-mediated oxidation of dibenzylamine to the corresponding imine (see: Jiang, G.; Chen, J.; Huang, J.-S.; Che, C.-M. Org. Lett. 2009, 11, 4568):
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35
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76149146497
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Using 4 under an oxygen atmosphere, we observed only 12% conversion of dibenzylamine to its imine after 12 h cf. TPP, O2, 10-14 h, In contrast, we found that TPP is capable of mediating the oxidative aza-Henry reaction of 1, but the reaction required 72 h for complete conversion compared with only 10 h under our conditions using 4. See the Supporting Information for further details
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2, 10-14 h). In contrast, we found that TPP is capable of mediating the oxidative aza-Henry reaction of 1, but the reaction required 72 h for complete conversion compared with only 10 h under our conditions using 4. See the Supporting Information for further details.
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36
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1H NMR analysis, but 12 was not stable under purification by chromatography.
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1H NMR analysis, but 12 was not stable under purification by chromatography.
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