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Ullmann diaryl ether synthesis: rate acceleration by 2,2,6,6-tetramethylheptane-3,5-dione.

Organic letters (2002-04-27)
Elizabeth Buck, Zhiguo Jake Song, David Tschaen, Peter G Dormer, R P Volante, Paul J Reider
ABSTRACT

[reaction: see text]. In the copper salt catalyzed ether formation from aryl bromides or iodides and phenols, 2,2,6,6-tetramethylheptane-3,5-dione (TMHD) was found to greatly accelerate the ordinarily difficult reaction, making it occur under more moderate temperatures and reaction times. A series of aryl halides and phenols were shown to form ethers in NMP as the solvent, cesium carbonate as the base, and CuCl and TMHD as the catalysts. The reaction was shown to tolerate electron-rich aryl bromides and electron-neutral phenols.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2,2,6,6-Tetramethyl-3,5-heptanedione, 98%
Supelco
2,2,6,6-Tetramethyl-3,5-heptanedione, for GC derivatization, LiChropur, ≥98.0%