Lewis acid promoted ruthenium(II)-catalyzed etherifications by selective hydrogenation of carboxylic acids/esters

Angewandte Chemie
Yuehui LiMatthias Beller

Abstract

Ethers are of fundamental importance in organic chemistry and they are an integral part of valuable flavors, fragrances, and numerous bioactive compounds. In general, the reduction of esters constitutes the most straightforward preparation of ethers. Unfortunately, this transformation requires large amounts of metal hydrides. Presented herein is a bifunctional catalyst system, consisting of Ru/phosphine complex and aluminum triflate, which allows selective synthesis of ethers by hydrogenation of esters or carboxylic acids. Different lactones were reduced in good yields to the desired products. Even challenging aromatic and aliphatic esters were reduced to the desired products. Notably, the in situ formed catalyst can be reused several times without any significant loss of activity.

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Citations

Oct 21, 2015·Journal of the American Chemical Society·Iván SorribesMatthias Beller
Dec 15, 2015·Angewandte Chemie·Markus MeureschJürgen Klankermayer
Jan 18, 2017·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Guillaume CompainElisabet Duñach
Feb 26, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Andreas PhanopoulosPhilip W Miller
Apr 1, 2018·Angewandte Chemie·Tobias BibergerBill Morandi
May 4, 2018·Angewandte Chemie·Patrick-Kurt DanneckerMichael A R Meier
Jul 6, 2016·Nature Communications·Kaiwu DongMatthias Beller
Jun 27, 2018·Chemistry : a European Journal·Lutz Greb
Jan 23, 2019·Organic & Biomolecular Chemistry·Joseph Becica, Graham E Dobereiner
Jul 25, 2019·ChemSusChem·Bernhard M StadlerJohannes G de Vries
Nov 12, 2015·Angewandte Chemie·Jose R Cabrero-AntoninoMatthias Beller
Dec 1, 2018·ChemistryOpen·Efimov IlyaLeonid Voskressensky
Nov 23, 2017·Chemical Science·Jose R Cabrero-AntoninoMatthias Beller
Jul 21, 2015·Angewandte Chemie·Xinjiang CuiMatthias Beller
Feb 23, 2021·Angewandte Chemie·Ursula BiermannJürgen O Metzger

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