Synthesis of ethers

Name Reactions

Reactions

Reductive Etherification

Protecting Groups

Allyl Ethers

Recent Literature

Nucleophilic fluorination using CsF or alkali metal fluorides was completed in short reaction time in the presence of [bmim][BF₄] affording the desired products without any byproducts. Facile nucleophilic substitutions such as halogenations, acetoxylation, nitrilation, and alkoxylations in the presence of ionic liquids provided the desired products in good yields.
D. W. Kim, C. E. Song, D. Y. Chi, J. Org. Chem., 2003, 68, 4281-4285.

A new synthetic method for the preparation of potassium organotrifluoroborates through nucleophilic substitution of potassium bromo- and iodomethyltrifluoroborates is described. Potassium halomethyltrifluoroborates have been prepared via in situ reaction of n-BuLi with dibromo- and diiodomethane, respectively, in the presence of trialkyl borates, followed by treatment with KHF₂.
G. A. Molander, J. Ham, Org. Lett., 2006, 8, 2031-2034.

A novel electrolytic system for non-Kolbe electrolysis based on the acid-base reaction between carboxylic acids and solid-supported bases in MeOH provide the corresponding methoxylated products in excellent yields. The acid-base reaction between carboxylic acids and solid-supported bases preferentially takes place to reduce the cell voltage in MeOH.
T. Tajima, H. Kurihara, T. Fuchigami, J. Am. Chem. Soc., 2007, 129, 6680-6681.

The combination of a copper-catalyzed C-O coupling reaction with a subsequent Claisen rearrangement allowed the generation of two adjacent quarternary stereocenters in a one-pot domino process. Furthermore, an experimentally simple stereoselective synthesis of of vinyl ethers is delineated using the same catalyst system.
G. Nordmann, S. L. Buchwald, J. Am. Chem. Soc., 2003, 125, 4978-4979.

A mild method for the trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed one-pot synthesis of homoallyl ethers from aldehydes has been developed in the ionic liquid 1-butyl-3-methylimidazolium trifluoromethanesulfonate ([bmim] [OTf]). The advantages of this method include the use of a recyclable ionic liquid, facile product isolation without employing excess organic solvent and elimination of an aqueous waste stream.
P. W. Anzalone, R. S. Mohan, Synthesis, 2005, 2661-2663.

P. W. Anzalone, R. S. Mohan, Synthesis, 2005, 2661-2663.

A Pd-catalysed termolecular allenylation cascade followed by a Ru catalysed RCM process affords a diverse range of Δ³-aryl/heteroaryl substituted five-seven membered nitrogen and oxygen heterocycles.
H. A. Dondas, B. Clique, B. Cetinkaya, R. Grigg, C. Kilner, J. Morris, V. Sridharan, Tetrahedron, 2005, 61, 10652-10666.

p-Toluenesulfonic acid efficiently catalyzes direct nucleophilic substitutions of the hydroxy groups of propargylic alcohols with a large variety of carbon- and heteroatom-centered nucleophiles. Reactions can be conducted under mild conditions and in air without the need for dried solvents.
R. Sanz, A. Martinez, J. M. Alvarez-Gutierrez, F. Rodriquez, Eur. J. Org. Chem., 2006, 1383-1386.

A general and efficient FeCl₃-catalyzed substitution reaction of propargylic alcohols with carbon- and heteroatom-centered nucleophiles such as allyl trimethylsilane, alcohols, aromatic compounds, thiols, and amides, forms new C-C, C-O, C-S and C-N bonds.
Z.-P. Zhan, J.-L. Yu, Y.-Y. Cui, R.-F. Yang, W.-Z. Yang, J.-P. Li, J. Org. Chem., 2006, 71, 8298-8301.

The preparation of diverse β-chloroethers, β-chloroacetates, and chlorohydrins is efficiently achieved under mild conditions by reaction of alkenes with trichloroisocyanuric acid in alcohols, acetic acid or aqueous acetone, respectively.
G. Fonseca Mendonça, A. Manzolillo Sanseverino, M. C. S. de Mattos, Synthesis, 2003, 45-48.