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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]

PMID: 18761437

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