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DOI: 10.1055/s-0028-1083589
An Efficient Ullmann-Type Cu-Catalyzed C-O Bond Formation
Contributor(s):Paul Knochel, Andrei GavryushinChangchun Institute of Applied Chemistry, P. R. of China and Institute for Diabetes Discovery, Branford, USA
An Efficient Ullmann-Type C-O Bond Formation Catalyzed by an Air-Stable Copper(I)-Bipyridyl Complex
J. Org. Chem. 2008, 73: 7814-7817
Publication History
Publication Date:
20 November 2008 (online)
Key words
Ullmann reaction - O-arylation - copper
Significance
Aryl ethers are important structural units in a number of biologically active substances and perspective compounds for material science. This method is using a relatively small amount of stable, inexpensive catalyst and displays a broad reaction scope. Aryl bromides can be used instead of more expensive iodides even for sterically hindered substrates.
Comment
The original conditions for synthesis of aryl ethers were published by Ullmann in 1903. Most of the recent methods use expensive and hygroscopic Cs2CO3 as a base. The use of K3PO4 and a simple bipyridyl ligand can be of great interest for industrial processes.
Review: For a review on the synthesis of aryl ethers and thioethers, see: S. V. Ley, A. W. Thomas Angew. Chem. Int. Ed. 2004, 42, 5400-5449.