Transition metals-catalyzed amination of biomass feedstocks for sustainable construction of N-heterocycles

Yan, Qiong; Wu, Xu; Jiang, Hao; Wang, Hao; Xu, Feng; Li, Hu; Zhang, Heng; Yang, Song

doi:10.1016/j.ccr.2023.215622

Cited by 60 publications

(25 citation statements)

References 388 publications

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“…However, the reaction process involves multi-electron transfer and generation of multiple by-products, leading to problems such as slow reactions, low energy utilization, and low output power. 4–6 To improve the electrochemical reaction rate, people have been trying to explore and develop efficient catalysts. 6–8 Catalysts can reduce the activation energy required for the reaction and can significantly increase the electrochemical reaction rate, which is key to enhancing the conversion efficiency of electrochemical devices.…”

Section: Introductionmentioning

confidence: 99%

“…4–6 To improve the electrochemical reaction rate, people have been trying to explore and develop efficient catalysts. 6–8 Catalysts can reduce the activation energy required for the reaction and can significantly increase the electrochemical reaction rate, which is key to enhancing the conversion efficiency of electrochemical devices. 9–11…”

Section: Introductionmentioning

confidence: 99%

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Application of 1D/2D carbon material supported metal nanoclusters for electrochemical conversion

Song,

Shi,

Liu

et al. 2024

Catal. Sci. Technol.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Application of 1D/2D carbon material supported metal nanoclusters for electrochemical conversion

Song,

Shi,

Liu

et al. 2024

Catal. Sci. Technol.

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“…The increasing energy demand and depleting fossil fuel supply have prompted extensive research to investigate sustainable biomass resources as viable alternatives. − Regarding this matter, fructose-derived 5-methyl furfural ( MF ) and its hydrogenated derivative, 5-methyl furfuryl alcohol ( MFA ), are proposed for biofuel development, serving as stable and versatile substrates with reduced oxygen content. They are vital intermediates for pharmaceuticals, food flavoring, agricultural chemicals, and biodiesel production, holding industrial significance.…”

Section: Introductionmentioning

confidence: 99%

Well-Defined Robust Imidazole-Based Metal–Ligand Cooperative Ru(II)-para-Cymene for Transfer Hydrogenation of Furanic Aldehydes Using Renewable Alcohols

Patil,

Pratihar

2024

ACS Sustainable Chem. Eng.

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The present study addresses the challenges in catalytic transfer hydrogenation using methanol/ethanol for converting biomass-derived furanic aldehydes to furfuryl alcohols. The introduction of air-stable Ru(II)-para-cymene catalysts with imidazole-based metal–ligand cooperativity represents a significant advancement. Spectroscopic, in situ monitoring, labeling, and DFT investigations reveal mechanistic details, highlighting the role of Ru–H generation through the dehydrogenation of Ru(II)-alkoxide intermediates. Hydride and proton transfers are facilitated by the interconvertible coordination mode of imidazole with Ru(II)–para-cymene, which is crucial for maintaining the catalyst’s efficiency and selectivity. Notably, the pK a of the N–H in coordinated imidazole significantly influences the reactivity, following a specific order depending on the attached heterocycle: imidazole > pyridine > thiazole. This order correlates well with the computed activation barrier for Ru–H generation. The catalyst exhibits ease of synthesis, stability in air and moisture, use of renewable hydrogen sources, excellent selectivity for aldehydes, applicability to various furanic aldehydes, and potential for large-scale processes. These features collectively contribute to the economic and sustainable nature of both the catalyst and the protocol, providing a valuable contribution to the field of catalytic transfer hydrogenation.

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“…An increasing concern over the depletion of global resources urges the adoption of renewable biomass utilization for the production of biofuels and bioproducts to protect the environment and mitigate climate change. − Biomass is considered as a carbon-neutral energy source, which can be used as the raw material for fine chemicals . Cellulose is a promising feedstock for bioenergy production with great potential in sustainable fuel and various biochemical synthesis .…”

Section: Introductionmentioning

confidence: 99%

Enhancing the Synergistic Effect of Bifunctional Pd-Based Catalyst by Phosphonic Acid for Cellobiose Conversion to Sorbitol

Shi,

Yang,

et al. 2024

ACS Sustainable Chem. Eng.

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Catalytic conversion of cellulosic biomass into polyols is an effective approach for biomass upgrading. However, the conversion involves cascade reactions which require various catalytic sites cooperation for activating specific steps, resulting in low efficiency. Here, we propose a bifunctional catalyst containing acid sites and hydrogenation capacity for polyol production with cellobiose as the model compound of cellulose. Phosphonic acids (PAs) containing either methyl (MPA) or aminomethyl (NH 2 MPA) tails were used to tune the Pd/Al 2 O 3 catalyst to form monolayers, thereby modulating the surface physiochemical properties and introducing multiple catalytic sites. An increasing ratio of PdO/Pd and a strong metal−support interaction were observed after PA modification, which could boost the hydrogenation activity for cellobiose. Furthermore, Pd/Al 2 O 3 -MPA exhibited excellent hydrolytic hydrogenation activity due to the increase of Lewis acid sites with good durability under hydrothermal conditions by MPA modification, achieving a 78.5% yield of sorbitol at 180 °C for 5 h. A plausible mechanism for enhancing the synergistic effect of Pd and support over Pd/Al 2 O 3 -MPA was also proposed. This investigation provides a novel strategy for rationally designing hydrothermally stable bifunctional catalysts to utilize biomass in a more effective way.

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Transition metals-catalyzed amination of biomass feedstocks for sustainable construction of N-heterocycles

Cited by 60 publications

References 388 publications

Application of 1D/2D carbon material supported metal nanoclusters for electrochemical conversion

Application of 1D/2D carbon material supported metal nanoclusters for electrochemical conversion

Well-Defined Robust Imidazole-Based Metal–Ligand Cooperative Ru(II)-para-Cymene for Transfer Hydrogenation of Furanic Aldehydes Using Renewable Alcohols

Enhancing the Synergistic Effect of Bifunctional Pd-Based Catalyst by Phosphonic Acid for Cellobiose Conversion to Sorbitol

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