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

A vast rate increase has been achieved by the use of high concentration
combined with sonication in the Mitsunobu reaction of phenols with alcohols
where at least one substrate is sterically demanding.
S. D. Lepore, Y. He,
J. Org. Chem., 2003, 68, 8261-8263.

Use of a solvent with greater density than the fluorous phase is an
alternative to the U-tube method in phase-vanishing reactions in cases where
both reactants are less dense than the fluorous phase. This method has
been successfully applied to the methylation of a phenol derivative with
dimethyl sulfate and to the m-CPBA-induced epoxidation of alkenes, N-oxide
formation from nitrogen-containing compounds, and S-oxide or sulfone
formation from organic sulfides.
N. K. Jana, J. G. Verkade, Org. Lett., 2003, 5,
3787-3790.

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 mild and efficient intermolecular addition of phenols and carboxylic acids
to olefins is catalyzed by Ph3PAuOTf.
C.-G. Yang, C. He, J. Am. Chem. Soc.,
2005,
127, 6966-6967.

A simple addition of phenols, carboxylic acids, and protected amines to
olefins can be catalyzed by triflic acid. A low concentration of triflic
acid and control of the reaction temperature help to tolerate functional
groups, such as methoxyl substitution on aromatics.
Z. Li, J. Zhang, C. Brouwer, C.-G. Yang, N. W. Reich, C. He, Org. Lett.,
2006,
8, 4175-4178.

An enantioselective and regioselective allylic etherification of various
sodium and lithium aryloxides with achiral (E)-cinnamyl and terminal
aliphatic allylic electrophiles in the presence of 2 mol% of an
iridium-phosphoramidite complex provides chiral allylic aryl ethers in high
yields and excellent levels of regio- and enantioselectivity.
F. Lopez, T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc., 2003,
125, 3426-3427.

The allylic amination and etherification of a broad range of allylic
carbonates occurred in high yields and with high regioselectivities and
enantioselectivities with an activated metallacyclic
iridium
catalyst containing a bis-naphthethylamino
group.
A. Leitner, C. Shu, J. F. Hartwig, Org. Lett., 2005,
7, 1093-1096.

