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For a review, see:, and references therein
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For a review, see: L.-C. Campeau, K. Fagnou, Chem. Commun. 2006, 1253-1264, and references therein.
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Chem. Commun
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Campeau, L.-C.1
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33644529707
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For a recent tandem reaction involving an intramolecular direct arylation with an aryl chloride, see
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For a recent tandem reaction involving an intramolecular direct arylation with an aryl chloride, see: J.-P. Leclerc, M. André, K. Fagnou, J. Org. Chem. 2006, 71, 1711-1714.
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34347266887
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For representative examples of elegant domino reactions involving direct arylation reactions with iodides and bromides, see: a G. Dyker, J. Körning, P. G. Jones, P. Bubenitschek, Angew. Chem. 1993, 105, 1805-1807;
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For representative examples of elegant domino reactions involving direct arylation reactions with iodides and bromides, see: a) G. Dyker, J. Körning, P. G. Jones, P. Bubenitschek, Angew. Chem. 1993, 105, 1805-1807;
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b) H. A. Wegner, L. T. Scott, A. de Meijere, J. Org. Chem. 2003, 68, 883-887;
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Campo, M.A.1
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d) F. Faccini, E. Motti, M. Catellani, J. Am. Chem. Soc. 2004, 126, 78-79;
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e) C. Bressy, D. Alberico, M. Lautens, J. Am. Chem. Soc. 2005, 127, 13148-13149;
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33646152128
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and references therein
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h) D. J. Cárdenas, B. Martin-Matute, A. M. Echavarren, J. Am. Chem. Soc. 2006, 128, 5033-5040, and references therein.
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Cárdenas, D.J.1
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26
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0000401303
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For a stepwise carbazole synthesis using 2-bromo-1-iodobenzene, see: a
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For a stepwise carbazole synthesis using 2-bromo-1-iodobenzene, see: a) T. Iwaki, A. Yasuhara, T. Sakamoto, J. Chem. Soc. Perkin Trans. 1 1999, 1505-1510;
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J. Chem. Soc. Perkin Trans. 1
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Iwaki, T.1
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27
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0037723821
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and references therein
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b) I. C. F. R. Ferreira, M.-J. R. P. Queiroz, G. Kirsch, Tetrahedron 2003, 59, 3737-3742, and references therein.
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Tetrahedron
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Ferreira, I.C.F.R.1
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Kirsch, G.3
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2-Chloro-1-iodoarenes were previously used for indole syntheses, which are based on a Sonogashira coupling and an amination reaction: a L. Ackermann, Org. Lett. 2005, 7, 439-442;
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2-Chloro-1-iodoarenes were previously used for indole syntheses, which are based on a Sonogashira coupling and an amination reaction: a) L. Ackermann, Org. Lett. 2005, 7, 439-442;
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31
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3843065849
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Selected recent palladium-catalyzed carbazole syntheses: a H.-J. Knölker, J. Knöll, Chem. Commun. 2003, 1170-1171;
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Selected recent palladium-catalyzed carbazole syntheses: a) H.-J. Knölker, J. Knöll, Chem. Commun. 2003, 1170-1171;
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32
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0142245953
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b) K. Nozaki, K. Takahashi, K. Nakano, T. Hiyama, H.-Z. Tang, M. Fujiki, S. Yamaguchi, K. Tamao, Angew. Chem. 2003, 115, 2097-2099;
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Angew. Chem. Int. Ed. 2003, 42, 2051-2053;
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c) W. C. P. Tsang, N. Zheng, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 14560-14561;
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Tsang, W.C.P.1
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34347249129
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and references therein
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d) M. P. Krahl, A. Jäger, T. Krause, H.-J. Knölker, Org. Biomol. Chem. 2006, 4, 3125-3219, and references therein.
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Org. Biomol. Chem
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Krahl, M.P.1
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Knölker, H.-J.4
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2NH led to 72% yield of isolated product.
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2NH led to 72% yield of isolated product.
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37
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34347272624
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3 as base and DMA as solvent gave only 6% conversion (GC analysis) to the desired product for the transformation described in Table 2, entry 3.
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3 as base and DMA as solvent gave only 6% conversion (GC analysis) to the desired product for the transformation described in Table 2, entry 3.
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38
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34347263706
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The regiochemistry of carbazoles 3 was unambiguously established by various 2D NMR experiments and a single-crystal X-ray diffraction analysis of 3b, 3k, 3m, 3o, and 3p.
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The regiochemistry of carbazoles 3 was unambiguously established by various 2D NMR experiments and a single-crystal X-ray diffraction analysis of 3b, 3k, 3m, 3o, and 3p.
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