Palladium-Catalyzed Method for the Synthesis of Carbazoles via Tandem C−H Functionalization and C−N Bond Formation

The development of a new method for the assembly of unsymmetrical carbazoles is reported. The strategy involves the selective intramolecular functionalization of an arene C−H bond and the formation of a new arene C−N bond. The substitution pattern of the carbazole product can be controlled by the de...

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Veröffentlicht in:Journal of organic chemistry 2008-10, Vol.73 (19), p.7603-7610
Hauptverfasser: Tsang, W. C. Peter, Munday, Rachel H, Brasche, Gordon, Zheng, Nan, Buchwald, Stephen L
Format: Artikel
Sprache:eng
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Zusammenfassung:The development of a new method for the assembly of unsymmetrical carbazoles is reported. The strategy involves the selective intramolecular functionalization of an arene C−H bond and the formation of a new arene C−N bond. The substitution pattern of the carbazole product can be controlled by the design of the biaryl amide substrate, and the method is compatible with a variety of functional groups. The utility of the new protocol was demonstrated by the concise synthesis of three natural products from commercially available materials.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo801273q