Highly Selective Room-Temperature Copper-Catalyzed C−N Coupling Reactions

Alexandr Shafir and Stephen L. Buchwald*
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139
J. Am. Chem. Soc., 2006, 128 (27), pp 8742–8743
DOI: 10.1021/ja063063b
Publication Date (Web): June 17, 2006
Copyright © 2006 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

Through the use of cyclic β-diketones as supporting ligands, the copper-catalyzed coupling of aryl iodides with aliphatic amines occurs at room temperature in as little as 1 h. These high reaction rates allow for the coupling of a wide range of aryl and heteroaryl iodides at room temperature. This method is highly tolerant of a number of reactive functional groups, including −Br and aromatic −NH2 as well as phenolic and aliphatic −OH. The high selectivity of the CuI−β-diketone catalyst for aliphatic amines represents a useful complement to the palladium-based methods.

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History

  • Published In Issue July 12, 2006
  • Received May 2, 2006

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