Palladium-Catalyzed Anilide ortho-Arylation and Subsequent One-Pot Cyclization to Phenanthridines

Dmitry Shabashov and Olafs Daugulis*
Department of Chemistry, University of Houston, Houston, Texas 77204
J. Org. Chem., 2007, 72 (20), pp 7720–7725
DOI: 10.1021/jo701387m
Publication Date (Web): September 7, 2007
Copyright © 2007 American Chemical Society
*

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

, olafs@uh.edu

Abstract

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The palladium-catalyzed direct arylation of anilides possessing several N-acyl substituents has been demonstrated. Removal of the acyl group by base hydrolysis allows a short and efficient synthesis of 2-aryl or 2,6-diarylanilines. The method is functional group tolerant and allows the presence of chloride and bromide substituents on both the anilide and aryl iodide coupling components. The arylation products can be converted to phenanthridines by the reaction with trifluoroacetic anhydride.

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History

  • Published In Issue September 28, 2007
  • Received June 26, 2007

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