Categories: C-O Bond Formation > Synthesis of ethers >
Reductive Etherification
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A well-defined cationic Ru-H complex catalyzes reductive etherification of
aldehydes and ketones with alcohols using water as the solvent and cheaply
available molecular hydrogen as the reducing agent to afford unsymmetrical
ethers in a highly chemoselective manner.
N. Kalutharage, C. S. Yi, Org. Lett.,
2015,
17, 1778-1781.
A readily accessible thiourea organocatalyst catalyzes reductive condensations
of alcohols with aldehydes/ketones to provide ethers without homocoupling of the
carbonyl component in the presence of HCl and 1,1,3,3-tetramethyldisiloxane as a
convenient reducing reagent. This strategy is applicable to challenging
substrate combinations and exhibits functional group tolerance.
C. Zhao, C. A. Sojdak, W. Myint, D. Seidel, J. Am. Chem. Soc., 2017,
139, 10224-10227.
A heterogeneous platinum catalyst efficiently mediates the reductive
etherification of ketones at ambient hydrogen pressure. In this transformation,
water is released as the only by-product, and this is trapped with molecular
sieves.
L. J. Gooßen, C. Linder, Synlett, 2006,
3489-3491.
A simple iron- and silyl chloride catalyzed reductive etherification enables the
preparation of symmetrical and nonsymmetrical ethers from various aldehydes and
ketones in the presence of triethylsilane as a reducing agent and catalytic
amounts of iron(III) oxo acetate and chloro(trimethyl)silane. The
reactions can be carried out at ambient temperatures in ethyl acetate as the
solvent.
R. Savela, R. Leino,
Synthesis, 2015, 47, 1749-1760.
Facile reductive etherification of carbonyl compounds
can be conveniently performed by reaction with triethylsilane and
alkoxytrimethylsilane catalyzed by iron(III) chloride. The corresponding alkyl
ethers, including benzyl and allyl ethers, of the reduced alcohols were obtained
in good to excellent yields under mild reaction conditions.
K. Iwanami, H. Seo, Y. Tobita, T. Oriyama, Synthesis, 2005,
183-186.
Medium-sized cyclic ethers have been effectively synthesized through
intramolecular reductive coupling of dialdehydes in the presence of a
hydrosilane and low loadings of AgNTf2 as catalyst at 25°C. The
catalytic system is also suitable for the coupling of two different
monoaldehydes to provide unsymmetrical ethers. This protocol features broad
functional group compatibility and high product diversity.
T. Liang, G. Dong, C. Li, X. Xu, Z. Xu, Org. Lett.,
2022, 24, 1817-1821.
Various silyl ethers were readily and efficiently transformed into the
corresponding alkyl ethers in high yields by the use of aldehydes combined
with triethylsilane in the presence of a catalytic amount of iron(III)
chloride.
K. Iwanami, K. Yano, T. Oriyama,
Synthesis, 2005, 2669-2672.
Aromatic aldehydes were easily converted to the corresponding ethers in
methanol or ethanol using decaborane at r.t. under nitrogen in high yields.
S. H. Lee, Y. J. Park, C. M. Yoon, Tetrahedron Lett., 1999, 40,
6049-6050.
Medium-sized cyclic ethers have been effectively synthesized through
intramolecular reductive coupling of dialdehydes in the presence of a
hydrosilane and low loadings of AgNTf2 as catalyst at 25°C. The
catalytic system is also suitable for the coupling of two different
monoaldehydes to provide unsymmetrical ethers. This protocol features broad
functional group compatibility and high product diversity.
T. Liang, G. Dong, C. Li, X. Xu, Z. Xu, Org. Lett.,
2022, 24, 1817-1821.