Journal of Organic Chemistry 2008-10-03

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

W C Peter Tsang, Rachel H Munday, Gordon Brasche, Nan Zheng, Stephen L Buchwald

Index: J. Org. Chem. 73(19) , 7603-10, (2008)

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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.