Transfer hydrogenation of levulinic acid from glycerol and ethanol using water-soluble iridium N-heterocyclic carbene complexes

Wang, Kai; Heltzel, Jacob; Sandefur, Evan; Culley, Keira; Lemcoff, N. Gabriel; Voutchkova‐Kostal, Adelina

doi:10.1016/j.jorganchem.2020.121310

Cited by 13 publications

(13 citation statements)

References 66 publications

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“…Recently, Voutchkova–Kostal group reported the water‐soluble iridium‐catalyzed transfer hydrogenation of levulinic acid using glycerol and EtOH under microwave heating conditions to afford GHV with TON of 101,000 (glycerol) and 7580 (EtOH), respectively. [ 26 ] Our catalytic conditions using Ir(triscarbene) catalysts and Ba(OH) 2 promoted these transformations with excellent TONs using various alcohols such as glycerol, PG, IPA, and EtOH.…”

Section: Resultsmentioning

confidence: 99%

“…[ 23,24 ] In contrast to the transfer hydrogenation of levulinic acid using formic acid, only a few alcohol‐mediated transfer hydrogenation reactions have been employed for the production of GVL. [ 25–27 ]…”

Section: Introductionmentioning

confidence: 99%

“…[23,24] In contrast to the transfer hydrogenation of levulinic acid using formic acid, only a few alcohol-mediated transfer hydrogenation reactions have been employed for the production of GVL. [25][26][27] Transfer hydrogenation has the benefits of avoiding the use of hydrogen at high pressures in favor of sustainable liquid hydrogen sources. [28] Thus, it is valuable to study efficient and sustainable transfer hydrogenation conditions for the synthesis of GVL from levulinic acid.…”

Section: Introductionmentioning

confidence: 99%

“…[29][30][31] Thereby, the Voutchkova-Kostal group reported the Ir-catalyzed transfer hydrogenation of levulinic acid using glycerol under microwave heating conditions with a good turnover number (TON) and turnover frequency (TOF). [26] Here, we report efficient Ir(triscarbene) catalysts for the transfer hydrogenation of levulinic acid to GVL in the presence of glycerol, propylene glycol (PG), ethylene glycol (EG), isopropanol (IPA), and ethanol (EtOH) with excellent TONs and TOFs. A TON of 500,000 (TOF of 170,000 h −1 ) was observed when using glycerol as a hydride source under conventional heating conditions (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

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Ir(triscarbene)‐catalyzed sustainable transfer hydrogenation of levulinic acid to γ‐valerolactone

Sung

Lee

Cheong

et al. 2020

Applied Organom Chemis

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Sustainable iridium‐catalyzed transfer hydrogenation using glycerol as the hydride source was employed to convert levulinic acid to γ‐valerolactone (GVL) with exceptionally high turnover numbers (TONs) (500,000) and turnover frequencies (TOFs) (170,000 h−1). The highly efficient triscarbene‐modified iridium catalysts demonstrated good catalytic activities with low catalyst loadings (0.7 ppm) and good recyclability with an accumulated TON of over two million in the fourth reaction. In addition to glycerol, propylene glycol (PG), ethylene glycol (EG), isopropanol (IPA), and ethanol (EtOH) successfully transferred hydrides to levulinic acid, producing GVL with TONs of 339,000 (PG), 242,000 (EG), 334,000 (IPA), and 208,000 (EtOH), respectively. Deuterium‐labeling experiments were conducted to gain insight into the reaction mechanism.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Ir(triscarbene)‐catalyzed sustainable transfer hydrogenation of levulinic acid to γ‐valerolactone

Sung

Lee

Cheong

et al. 2020

Applied Organom Chemis

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“…In addition to the TH of aldehydes, ketones, imines, and olefins, glycerol has also been utilized for the TH of levulinic acid which can be derived from biomass. Recently, Voutchkova‐Kosta reported highly active catalysts based on iridium N‐heterocyclic carbene (NHC) complex for the TH of levulinic acid to Y‐ hydroxyvaleric acid (GHV) using glycerol as a hydrogen donor under basic conditions (KOH) at 150 °C [204] . A quantitative yield of GHV was obtained using just 1 ppm of catalyst Ir‐13 (Figure 11) exhibiting a TON of 101,100 and TOF of 50,550 h −1 .…”

Section: Dehydrogenation Of Glycerolmentioning

confidence: 99%

Homogeneous (De)hydrogenative Catalysis for Circular Chemistry – Using Waste as a Resource

Kumar

Gao

2020

ChemCatChem

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Increasing production and usage of several consumer products and energy sources have resulted in the accumulation of a substantial amount of waste products that are toxic and/or difficult to biodegrade, thus creating a severe threat to our planet. With the recently advocated concepts of circular chemistry, an attractive approach to tackle the challenge of chemical waste reduction is to utilize these waste products as feedstocks for the production of useful chemicals. Catalytic (de)hydrogenation is an atom‐economic, green and sustainable approach in organic synthesis, and several new environmentally benign transformations have been reported using this strategy in the past decade, especially using well‐defined transition metal complexes as catalysts. These discoveries have demonstrated the impact and untapped potential of homogeneous (de)hydrogenative catalysis for the purpose of converting chemical wastes into useful resources. Four types of chemical waste that have been (extensively) studied in recent years for their chemical transformations using homogeneous catalytic (de)hydrogenation are CO2, N2O, plastics, and glycerol. This review article highlights how these chemical wastes can be converted to useful feedstocks using (de)hydrogenative catalysis mediated by well‐defined transition metal complexes and summarizes various types of homogeneous catalysts discovered for this purpose in recent years. Moreover, with examples of hydrogenative depolymerization of plastic waste and the production of virgin plastic via dehydrogenative pathways, we emphasize the potential applications of (de)hydrogenation reactions to facilitate closed‐loop production cycles enabling a circular economy.

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Transition‐Metal‐Catalysed Transfer Hydrogenation Reactions with Glycerol and Carbohydrates as Hydrogen Donors

Ansari,

Anshika,

Sortais

et al. 2024

Eur J Org Chem

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Catalytic transfer hydrogenation is a practical approach for the reduction of various unsaturated compounds and an alternative to pressurised hydrogenation and traditional metal hydride reagents. Among the various hydrogen donors, biomass such as glycerol and carbohydrates received considerable attention for the reduction reactions due to their non‐toxic, eco‐friendly and renewable nature. The present review addresses the development of homogeneous and heterogeneous catalysts for the transfer hydrogenation of carbonyl compounds, alkenes, alkynes, nitro compounds, CO2 etc. using glycerol and carbohydrates as potential hydrogen donors.

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Transfer hydrogenation of levulinic acid from glycerol and ethanol using water-soluble iridium N-heterocyclic carbene complexes

Cited by 13 publications

References 66 publications

Ir(triscarbene)‐catalyzed sustainable transfer hydrogenation of levulinic acid to γ‐valerolactone

Ir(triscarbene)‐catalyzed sustainable transfer hydrogenation of levulinic acid to γ‐valerolactone

Homogeneous (De)hydrogenative Catalysis for Circular Chemistry – Using Waste as a Resource

Transition‐Metal‐Catalysed Transfer Hydrogenation Reactions with Glycerol and Carbohydrates as Hydrogen Donors

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