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Synthesis of aryl ethers

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Protective Groups


Allyl Ethers


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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.