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Palladium-catalyzed method for the synthesis of carbazoles via tandem C-H functionalization and C-N bond formation.


ABSTRACT: 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.

SUBMITTER: Tsang WC 

PROVIDER: S-EPMC2748774 | biostudies-literature | 2008 Oct

REPOSITORIES: biostudies-literature

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Palladium-catalyzed method for the synthesis of carbazoles via tandem C-H functionalization and C-N bond formation.

Tsang W C Peter WC   Munday Rachel H RH   Brasche Gordon G   Zheng Nan N   Buchwald Stephen L SL  

The Journal of organic chemistry 20080829 19


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 product  ...[more]

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