Palladium-Catalyzed Amination of Aryl Nonaflates

Kevin W. Anderson, Maria Mendez-Perez, Julian Priego, and Stephen L. Buchwald*
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139
J. Org. Chem., 2003, 68 (25), pp 9563–9573
DOI: 10.1021/jo034962a
Publication Date (Web): November 13, 2003
Copyright © 2003 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.

, sbuchwal@mit.edu

Abstract

Abstract Image

The first detailed study of the palladium-catalyzed amination of aryl nonaflates is reported. Use of ligands 2−4 and 6 allows for the catalytic amination of electron-rich and -neutral aryl nonaflates with both primary and secondary amines. With use of Xantphos 5, the catalytic amination of a variety of functionalized aryl nonaflates resulted in excellent yields of anilines; even 2-carboxymethyl aryl nonaflate is effectively coupled with a primary alkylamine. Moderate yields were obtained when coupling halo-aryl nonaflates with a variety of amines, where in most cases the aryl nonaflate reacted in preference to the aryl halide. Overall, aryl nonaflates are an effective alternative to triflates in palladium-catalyzed C−N bond-forming processes due to their increased stability under the reaction conditions.

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History

  • Published In Issue December 12, 2003
  • Received July 3, 2003

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