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

Yuehui Li, Christoph Topf, Xinjiang Cui, Kathrin Junge, Matthias Beller

Research output: Contribution to journalArticlepeer-review

80 Scopus citations

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. An assist from Al: A bifunctional catalyst system consisting of a Ru/phosphine complex and aluminum triflate allows selective hydrogenation of esters to ethers. A variety of lactones were reduced to the desired products in good yields. The catalyst further provides a general method for the reduction of linear esters and reductive etherification of carboxylic acids with alcohols.

Original languageEnglish
Pages (from-to)5196-5200
Number of pages5
JournalAngewandte Chemie International Edition in English
Volume54
Issue number17
DOIs
StatePublished - 20 Apr 2015
Externally publishedYes

Keywords

  • Lewis acids
  • ethers
  • homogeneous catalysis
  • hydrogenation
  • ruthenium

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