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Palladium-catalyzed synthesis of pyrrole-, indole- and phenanthridine-fused polycyclic aromatic compounds from ortho-dihaloarenes ( Dissertationsschrift )

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Convenient palladium-catalyzed syntheses of polycyclic nitrogen heterocycles from ortho-dihaloarenes were developed. First, syntheses of pyrrole-fused derivatives via domino C-C/C-N coupling of ortho-dihaloarenes with imines were accomplished. Employment of ortho-dihaloarenes for sequential regioselective Suzuki reaction/double C-N coupling afforded corresponding indole-fused structures. Finally, syntheses of previously unexplored phenanthridine-fused architectures by regioselective Sonogashira reaction followed by domino or one-pot C-N coupling/hydroamination/C-H arylation were described.<eng>

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