Categories: C-O Bond Formation >
Synthesis of aryl ethers
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Recent Literature

Self-assembled octanuclear copper clusters catalyzed
the coupling of aryl iodides with alcohols under mild
conditions. Reactions involving low catalyst loadings (0.4%) and tetrahydrofurfuryl alcohol were typically
complete in 4-8 h at 110°C using an oil bath or 1-3 h with microwave heating.
G. F. Manbeck, A. J. Lipman, R. A. Stockland, A. L. Freidl, A. F. Hasler, J.
J. Stone, I. A. Guzei, J. Org. Chem., 2005,
70, 244-250.

Ullmann-type coupling reactions of aryl iodides and aliphatic alcohols occur at
110 °C with N,N-dimethylglycine as the ligand, giving aryl alkyl ethers
in high yields.
H. Zhang, D. Ma, W. Cao, Synlett, 2007, 243-246.

A simple and mild coupling method of aryl iodides and aliphatic alcohols,
which does not require alkoxide bases, can be performed in neat alcohol or
toluene as solvent. An optically active benzylic alcohol underwent the reaction
with complete retention of configuration.
M. Wolter, G. Nordmann, G. E. Job, S. L. Buchwald, Org.
Lett., 2002, 4, 973-976.

A one-pot method for the preparation of alkyl aryl ethers from aryl halides
and the preparation of substituted benzofurans via a Pd-catalyzed phenol
formation/cyclization protocol starting from 2-chloroaryl alkynes are
described.
K. W. Anderson, T. Ikawa, R. E. Tundel, S. L. Buchwald, J. Am. Chem. Soc., 2006,
128, 10694-10695.

A palladium-catalyzed synthesis of aryl tert-butyl ethers from a
variety of unactivated aryl bromides or chlorides is described. The ether
products, which are precursors to phenols, are obtained in very good yield
in the presence of air-stable dialkylphosphinobiphenyl ligands.
C. A. Parrish, S. L. Buchwald, J. Org. Chem, 2001,
66, 2498-2500.

