Palladium-catalyzed hydrogenation with use of ionic liquid bis(2-hydroxyethyl)ammonium formate [BHEA][HCO2] as a solvent and hydrogen source

Hideyuki Suzuki, Seiki Yoshioka, Ami Igesaka, Hiromi Nishioka, Yasuo Takeuchi

Research output: Contribution to journal › Article

3 Citations (Scopus)

Abstract

We designed ionic liquid bis(2-hydroxyethyl)ammonium formate [BHEA][HCO2] for use as a solvent and hydrogen donor for hydrogenation. Catalytic hydrogenation of aromatic ketones, nitro groups, and olefins with PdCl2 in [BHEA][HCO2] generated the corresponding reduction products. Selective reduction of aromatic ketones over aliphatic ketones was observed. Hydrogenolysis of benzyl ethers and benzyl amines also proceeded. All these reactions were successfully carried out in good to excellent yields under mild and nonflammable conditions. In addition, the ionic liquid and Pd source can be reused several times.

Original languageEnglish
Pages (from-to)6399-6403
Number of pages5
JournalTetrahedron
Volume69
Issue number31
DOIs
Publication statusPublished - Aug 5 2013

Fingerprint

formic acid
Ionic Liquids
Hydrogenation
Palladium
Ketones
Hydrogen
Hydrogenolysis
Ethers
Alkenes
Amines

Keywords

  • Aromatic ketones
  • Hydrogenation
  • Ionic liquids
  • Nonflammability
  • Reuse

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Palladium-catalyzed hydrogenation with use of ionic liquid bis(2-hydroxyethyl)ammonium formate [BHEA][HCO2] as a solvent and hydrogen source. / Suzuki, Hideyuki; Yoshioka, Seiki; Igesaka, Ami; Nishioka, Hiromi; Takeuchi, Yasuo.

In: Tetrahedron, Vol. 69, No. 31, 05.08.2013, p. 6399-6403.

Research output: Contribution to journal › Article

Suzuki, H, Yoshioka, S, Igesaka, A, Nishioka, H & Takeuchi, Y 2013, 'Palladium-catalyzed hydrogenation with use of ionic liquid bis(2-hydroxyethyl)ammonium formate [BHEA][HCO2] as a solvent and hydrogen source', Tetrahedron, vol. 69, no. 31, pp. 6399-6403. https://doi.org/10.1016/j.tet.2013.05.103
Suzuki H, Yoshioka S, Igesaka A, Nishioka H, Takeuchi Y. Palladium-catalyzed hydrogenation with use of ionic liquid bis(2-hydroxyethyl)ammonium formate [BHEA][HCO2] as a solvent and hydrogen source. Tetrahedron. 2013 Aug 5;69(31):6399-6403. https://doi.org/10.1016/j.tet.2013.05.103
Suzuki, Hideyuki ; Yoshioka, Seiki ; Igesaka, Ami ; Nishioka, Hiromi ; Takeuchi, Yasuo. / Palladium-catalyzed hydrogenation with use of ionic liquid bis(2-hydroxyethyl)ammonium formate [BHEA][HCO2] as a solvent and hydrogen source. In: Tetrahedron. 2013 ; Vol. 69, No. 31. pp. 6399-6403.
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