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Volumn 350, Issue 3, 2008, Pages 465-470

Auto-tandem catalysis: Synthesis of substituted 11H-indolo [3,2-c]quinolines via palladium-catalyzed intermolecular C-N and intramolecular C-C bond formation

Author keywords

Amination; C H activation; Malaria; Palladium; Tandem catalysis

Indexed keywords


EID: 53849100355     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700328     Document Type: Article
Times cited : (59)

References (43)
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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.
    • 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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    • 4 base combination.
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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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