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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.


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.