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

doi:10.1016/j.tet.2013.05.103

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 › peer-review

4 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 language	English
Pages (from-to)	6399-6403
Number of pages	5
Journal	Tetrahedron
Volume	69
Issue number	31
DOIs	https://doi.org/10.1016/j.tet.2013.05.103
Publication status	Published - Aug 5 2013

Keywords

Aromatic ketones
Hydrogenation
Ionic liquids
Nonflammability
Reuse

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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

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.",

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author = "Hideyuki Suzuki and Seiki Yoshioka and Ami Igesaka and Hiromi Nishioka and Yasuo Takeuchi",

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T1 - Palladium-catalyzed hydrogenation with use of ionic liquid bis(2-hydroxyethyl)ammonium formate [BHEA][HCO2] as a solvent and hydrogen source

AU - Suzuki, Hideyuki

AU - Yoshioka, Seiki

AU - Igesaka, Ami

AU - Nishioka, Hiromi

AU - Takeuchi, Yasuo

PY - 2013/8/5

Y1 - 2013/8/5

N2 - 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.

AB - 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.

KW - Aromatic ketones

KW - Hydrogenation

KW - Ionic liquids

KW - Nonflammability

KW - Reuse

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