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For some recent examples on auto-tandem catalysis, see: a) K. T. J. Loones, B. U. W. Maes, R. A. Dommisse, G. L. F. Lemière, Chem. Commun. 2004, 2466-2467;
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For carbazole synthesis via Pd-catalyzed intramolecular arylation of N-aryl-2-chloroanilines, see: a L.-C. Campeau, P. Thansandote, K. Fagnou, Org. Lett. 2005, 7, 1857-1860;
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0000401303
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for carboline synthesis via Pd-catalyzed intramolecular arylation of N-azaheteroaryl-2-bromoanilines and N-(o-bromoazaheteroaryl)anilines, see: b) T. Iwaki, A. Yasuhara, T. Sakamoto, J. Chem. Soc., Perkin Trans. 1 1999, 1505-1510.
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for carboline synthesis via Pd-catalyzed intramolecular arylation of N-azaheteroaryl-2-bromoanilines and N-(o-bromoazaheteroaryl)anilines, see: b) T. Iwaki, A. Yasuhara, T. Sakamoto, J. Chem. Soc., Perkin Trans. 1 1999, 1505-1510.
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For carbazole synthesis via auto-tandem consecutive Buchwald-Hartwig reaction and Pd-catalyzed intramolecular arylation, see: a) R. B. Bedford, C. S. J. Cazin, Chem. Commun. 2002, 2310-2311;
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For carbazole synthesis via auto-tandem consecutive Buchwald-Hartwig reaction and Pd-catalyzed intramolecular arylation see: L. Ackermann, A. Althammer, Angew. Chem. 2007, 119, 1652;
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Angew. Chem. Int. Ed. 2007, 46, 1627; this paper also contains one example dealing with the synthesis of an N-substituted α-carboline [9-phenyl-3-(trifluoromethyl)-9H-pyrido[2,3-b]- indole] via auto-tandem catalysis. It is not clear if the protocols described can be used for the synthesis of N-unsubstituted α-carbolines.
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Angew. Chem. Int. Ed. 2007, 46, 1627; this paper also contains one example dealing with the synthesis of an N-substituted α-carboline [9-phenyl-3-(trifluoromethyl)-9H-pyrido[2,3-b]- indole] via auto-tandem catalysis. It is not clear if the protocols described can be used for the synthesis of N-unsubstituted α-carbolines.
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G. Rombouts, B. U. W. Maes, T. H. M. Jonckers, K. T. J. Loones, Org. Synth. 2007, 84, 215-221. Important general remarks should be made about 'base effects' in Pd-catalyzed reactions involving deprotonations in the rate-determining step of the catalytic cycle. If one wants to compare absolute amounts of base used for different bond forming reactions e.g, C-N, described in separate publications, one has to be sure that the base particle size distribution/total contact surface area was the same. Even if two teams buy the same quality of base from the same chemical supplier, it is highly doubtful that this requirement is fulfilled as they most probably received base from another lot. The stirring speed of the reaction should also be similar and therefore controlled as an interphase deprotonation mechanism will be seriously influenced by this factor. When no fundamental comparisons of different reactions are aimed, the base can be used as such if the total co
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[13d]
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