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Article

Effect of Solvents on Electrogenerated Base-Driven Transfer Hydrogenation Reactions

by
Jing-Wei Zhu
1,
Meng-Han Li
1,
Feng Zhang
1,
Ya-Li Wang
1,2,
Jia-Xing Lu
1,3 and
Huan Wang
1,3,*
1
Key Laboratory of Petroleum Molecular & Process Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China
2
College of Chemistry and Chemical Engineering, Ningxia Normal University, Guyuan 756099, China
3
Institute of Eco-Chongming, 20 Cuiniao Road, Chenjia Town, Chongming District, Shanghai 202162, China
*
Author to whom correspondence should be addressed.
Molecules 2025, 30(4), 910; https://doi.org/10.3390/molecules30040910
Submission received: 14 January 2025 / Revised: 9 February 2025 / Accepted: 13 February 2025 / Published: 15 February 2025
(This article belongs to the Special Issue Green Catalysis Technology for Sustainable Energy Conversion)
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Abstract

Transfer hydrogenation is a crucial technology for synthesizing fine chemicals and pharmaceuticals, offering improved safety and convenience over traditional hydrogen methods, although it typically requires external bases. While isopropanol is commonly used as a hydrogen source, methanol is superior but faces challenges due to its high dehydrogenation energy barrier, limiting its use under mild conditions. This study focuses on investigating the differences in the electrogenerated base-driven transfer hydrogenation of aromatic ketones in isopropanol and methanol solvents, using Mn(CO)₅Br and cyclohexanediamine derivatives as the catalyst. The research demonstrates that high enantiomeric excess (ee) values were obtained in isopropanol in the presence of chiral Mn-based catalysts, while only racemic products were observed in methanol. The results indicate a strong dependence of the catalytic pathway on the choice solvent: in isopropanol, the catalyst operates via a metal–ligand cooperative transfer hydrogenation, resulting in high ee values, whereas in methanol, transfer hydrogenation occurs through metal hydride transfer with no stereoselectivity.
Keywords: transfer hydrogenation; electrogenerated base; solvent effect; manganese catalysts; aromatic ketones transfer hydrogenation; electrogenerated base; solvent effect; manganese catalysts; aromatic ketones
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MDPI and ACS Style

Zhu, J.-W.; Li, M.-H.; Zhang, F.; Wang, Y.-L.; Lu, J.-X.; Wang, H. Effect of Solvents on Electrogenerated Base-Driven Transfer Hydrogenation Reactions. Molecules 2025, 30, 910. https://doi.org/10.3390/molecules30040910

AMA Style

Zhu J-W, Li M-H, Zhang F, Wang Y-L, Lu J-X, Wang H. Effect of Solvents on Electrogenerated Base-Driven Transfer Hydrogenation Reactions. Molecules. 2025; 30(4):910. https://doi.org/10.3390/molecules30040910

Chicago/Turabian Style

Zhu, Jing-Wei, Meng-Han Li, Feng Zhang, Ya-Li Wang, Jia-Xing Lu, and Huan Wang. 2025. "Effect of Solvents on Electrogenerated Base-Driven Transfer Hydrogenation Reactions" Molecules 30, no. 4: 910. https://doi.org/10.3390/molecules30040910

APA Style

Zhu, J.-W., Li, M.-H., Zhang, F., Wang, Y.-L., Lu, J.-X., & Wang, H. (2025). Effect of Solvents on Electrogenerated Base-Driven Transfer Hydrogenation Reactions. Molecules, 30(4), 910. https://doi.org/10.3390/molecules30040910

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