Novel Electron-Rich Bulky Phosphine Ligands Facilitate the Palladium-Catalyzed Preparation of Diaryl Ethers

A general method for the palladium-catalyzed formation of diaryl ethers is described. Electron-rich, bulky aryldialkylphosphine ligands, in which the two alkyl groups are either tert-butyl or 1-adamantyl, are the key to the success of the transformation. A wide range of electron-deficient, electroni...

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Bibliographic Details
Published in:Journal of the American Chemical Society 1999-05, Vol.121 (18), p.4369-4378
Main Authors: Aranyos, Attila, Old, David W, Kiyomori, Ayumu, Wolfe, John P, Sadighi, Joseph P, Buchwald, Stephen L
Format: Article
Language:English
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Summary:A general method for the palladium-catalyzed formation of diaryl ethers is described. Electron-rich, bulky aryldialkylphosphine ligands, in which the two alkyl groups are either tert-butyl or 1-adamantyl, are the key to the success of the transformation. A wide range of electron-deficient, electronically neutral and electron-rich aryl bromides, chlorides, and triflates can be combined with a variety of phenols with the use of sodium hydride or potassium phosphate as base in toluene at 100 °C. The bulky yet basic nature of the phosphine ligand is thought to be responsible for increasing the rate of reductive elimination of the diaryl ether from palladium.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja990324r