Ketone transfer hydrogenation reactions catalyzed by catalysts based on a phosphinite ligand

Abstract

Reaction of (±)-1-(2-furyl) ethanol with an equivalent Ph₂PCl in the presence of Et₃N proceeds in dry toluene under an argon atmosphere to give 1-(furan-2-yl)ethyl diphenylphosphinite (1) in good yield. Mononuclear complexes [dichloro(η⁶-p-cymene)(1-furan-2-ylethyl diphenylphosphinite)ruthenium(II)] (2), [dichloro(η⁶-benzene)(1-furan-2-ylethyl diphenylphosphinite)ruthenium(II)] (3), [chloro(η⁴-1,5-cyclooctadiene)(1-furan-2-ylethyl diphenylphosphinite)rhodium(I)] (4) and [dichloro(η⁵-pentamethylcyclopentadienyl)(1-furan-2-ylethyl diphenylphosphinite)iridium(III)] (5) were synthesized and characterized by microanalysis, infrared, MS, and NMR spectroscopies. The complexes are employed as catalysts in transfer hydrogenation of aromatic ketones. The complexes catalyzed reduction of a variety of aromatic ketone substrates bearing electron-withdrawing or donating substituents with very high conversion rates (up to 99%); 5 was the most efficient catalyst for the transfer hydrogenation of ketones.

Graphical Abstract

Keywords:

• Transfer hydrogenation
• iridium
• ketone
• phosphinite ligand
• transition metal

Acknowledgements

The research is funded by the Science Committee of the Ministry of Education and Science of the Republic of Kazakhstan (Grant No: AP08857516). Partial support of this work by Dicle University (Project number: FEN.20.003) is gratefully acknowledged.

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

The research is funded by the Science Committee of the Ministry of Education and Science of the Republic of Kazakhstan (Grant No: AP08857516). Partial support of this work by Dicle University (Project number: FEN.20.003) is gratefully acknowledged.