Lewis acid promoted ruthenium(II)-catalyzed etherifications by selective hydrogenation of carboxylic acids/esters.
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.
Leibniz-Institut für Katalyse e.V. Albert-Einstein-Str. 29a, 18059 Rostock (Germany) http://www.catalysis.de.
Yuehui
Y
Li
Christoph
C
Topf
Xinjiang
X
Cui
Kathrin
K
Junge
Matthias
M
Beller
D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry; D004952:Esters; D004987:Ethers / Q000138:chemical synthesis / Q000737:chemistry*; D006865:Hydrogenation; D058116:Lewis Acids / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry*
D002264:Carboxylic Acids; D056831:Coordination Complexes; D004952:Esters; D004987:Ethers; D058116:Lewis Acids; D008698:Mesylates; D010720:Phosphines; D012428:Ruthenium; C044646:phosphine; C012077:trifluoromethanesulfonic acid
Lewis acids; ethers; homogeneous catalysis; hydrogenation; ruthenium