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Synfacts 2006(2): 0110-0110  
DOI: 10.1055/s-2005-924823
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Carbazoles by Tandem C-H Activation and Buchwald-Hartwig Amination

Contributor(s): V. Snieckus, Oleg M. Demchuk
W. C. P. Tsang, N. Zheng, S. L. Buchwald*
Massachusetts Institute of Technology, Cambridge, USA
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Publikationsdatum:
23. Januar 2006 (online)

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Significance

A highly efficient synthetic route to substituted carbazoles is reported. Starting from readily available 2-acetamidobyphenyls, the reaction proceeds via a tandem palladium-catalyzed C-H activation, Buchwald-Hartwig amination and Wacker reoxidation process under mild conditions to give a variety of substituted carbazoles in 41-98% yields with excellent regioselectivities. A simple plausible mechanism involving intermediates A and B has been suggested.