Ir‐Catalyzed Transfer Hydrogenation and Alkylation of Aldehydes and Ketones Using Ethanol as the Hydrogen Source

Kuram, Malleswara Rao

doi:10.1002/ejoc.202201344

Eur J Org Chem

2023

DOI: 10.1002/ejoc.202201344

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Ir‐Catalyzed Transfer Hydrogenation and Alkylation of Aldehydes and Ketones Using Ethanol as the Hydrogen Source

Malleswara Rao Kuram

Abstract: Bio-derived ethanol is a promising green and sustainable hydrogen-donor solvent. Herein, we have developed Ir-catalyzed transfer hydrogenation of ketones and aldehydes using ethanol as a hydrogen source with amides as simple ligands.Furthermore, the alkylation of ketones and tandem alkylation/ transfer hydrogenation of acetophenones is reported with ethanol.

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Cited by 5 publications

References 74 publications

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Bidentate Ru(II)‐NC Complexes as Catalysts for Transfer Hydrogenation of Ketones with Ethanol

Li,

Lian,

Wang

et al. 2024

Asian J Org Chem

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We developed a bidentate Ru(II)‐NC‐catalyzed transfer hydrogen reaction of ketones using ethanol (EtOH) as the hydrogen source under a weak base condition. The control experiments suggested that the reaction proceeds via the Ru‐H mechanism and yields ethyl acetate as the only byproduct. The deuterium‐labeling experiments further showed that hydrogen evolved from the CH2 and OH groups. The results provide a new weak base system for the transfer hydrogen reaction of ketones using ethanol as the hydrogen donor.

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Bidentate Ru(II)‐NC Complexes as Catalysts for Transfer Hydrogenation of Ketones with Ethanol

Li,

Lian,

Wang

et al. 2024

Asian J Org Chem

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Sustainable and selective transfer hydrogenation using waste shrimp shell‐based tetrazene‐Ru (II) para‐cymene catalyst with ethanol as a hydrogen source

Patil,

Shelte,

Biradar

et al. 2023

Applied Organom Chemis

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Sustainable chemical research emphasizes chitosan‐based catalysts and the need to explore the direct utilization of waste shrimp shells, whereas the use of ethanol as a hydrogen source in transfer hydrogenation is less explored due to its unfavorable redox potential, higher energy barriers, generation of reactive intermediates, and catalyst poising via metal carbonyl species or decarbonylation. Herein, we disclosed an efficient synthetic approach, conducted at ambient temperature, for surface functionalization of waste shrimp shells with 3‐(3,5‐dimethyl‐1H‐pyrazol‐1‐yl)‐1,2,4,5‐tetrazine (DMPZ‐Tz) via nucleophilic substitution using 3,6‐bis(3,5‐dimethyl‐1H‐pyrazol‐1‐yl)‐1,2,4,5‐tetrazine (BDMPZ‐Tz). This method results in a color change and a 75% increase in surface nitrogen content, eliminating the need for multiple syntheses and harsh reaction conditions. We utilized the strong coordination property between DMPZ‐Tz and [Ru(p‐cym)Cl2]2/RuCl3.3H2O to develop ruthenium‐embedded transfer hydrogenation catalysts supported on shrimp shells. These catalysts were employed for the selective transfer hydrogenation of unsaturated carbonyl/aldehydes to saturated carbonyl/alcohols, utilizing ethanol as the hydrogen source and potassium carbonate as the base. The performance, selectivity, and reusability of the catalyst were thoroughly assessed through spectroscopic studies, in‐situ monitoring of the reaction progress, initial rate kinetics, and control experiments. The obtained results strongly indicated that the anchoring of DMPZ‐Tz played a crucial role in achieving superior performance compared with catalysts synthesized without it or utilizing its homogeneous counterparts. The catalyst exhibits efficient reactivity, selectivity, and broad substrate scope.

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Ethanol as hydrogen donor: An efficient transfer hydrogenation of aldehydes, ketones, and nitroarenes with H-bonded Ru(II)-N-heterocyclic iminium complex

Revathi,

Ghatak

2024

Journal of Catalysis

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Ir‐Catalyzed Transfer Hydrogenation and Alkylation of Aldehydes and Ketones Using Ethanol as the Hydrogen Source

Cited by 5 publications

References 74 publications

Bidentate Ru(II)‐NC Complexes as Catalysts for Transfer Hydrogenation of Ketones with Ethanol

Bidentate Ru(II)‐NC Complexes as Catalysts for Transfer Hydrogenation of Ketones with Ethanol

Sustainable and selective transfer hydrogenation using waste shrimp shell‐based tetrazene‐Ru (II) para‐cymene catalyst with ethanol as a hydrogen source

Ethanol as hydrogen donor: An efficient transfer hydrogenation of aldehydes, ketones, and nitroarenes with H-bonded Ru(II)-N-heterocyclic iminium complex

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