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Communication

Combined C−H Functionalization/C−N Bond Formation Route to Carbazoles

Supporting Info

W. C. Peter Tsang, Nan Zheng, and Stephen L. Buchwald*

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139

J. Am. Chem. Soc., 2005, 127 (42), pp 14560–14561

DOI: 10.1021/ja055353i

Publication Date (Web): October 4, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, sbuchwal@mit.edu

Abstract

A new method in which a series of substituted carbazoles is efficiently produced by the combination of an amide and an arene is described. The key feature of this method is the palladium-catalyzed tandem directed C−H functionalization and amide arylation. The method tolerates substitution on either ring of the biaryl amide substrates, and the products can be assembled in a simple two-step protocol from readily available reagents. The Pd(0) species generated are reoxidized to Pd(II) in the presence of Cu(OAc)₂ and an atmosphere of oxygen.

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History

Published In Issue October 26, 2005
Received August 5, 2005

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Communication

Combined C−H Functionalization/C−N Bond Formation Route to Carbazoles