Tsang W C Peter, Munday Rachel H, Brasche Gordon, Zheng Nan, Buchwald Stephen L
Department of Chemistry, Massachusetts Institute of Technology Cambridge, Massachusetts 02139, USA.
J Org Chem. 2008 Oct 3;73(19):7603-10. doi: 10.1021/jo801273q. Epub 2008 Aug 29.
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.