1. Amino acid-functionalized multi-walled carbon nanotubes: A metal-free chiral catalyst for the asymmetric electroreduction of aromatic ketones
- Author
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Ying-Na Yue, Li Liu, Huan Wang, Jia-Xing Lu, Qiao-Li Hu, and Wang-Jun Meng
- Subjects
Trifluoromethyl ,General Chemical Engineering ,Alcohol ,02 engineering and technology ,010402 general chemistry ,021001 nanoscience & nanotechnology ,01 natural sciences ,0104 chemical sciences ,Catalysis ,chemistry.chemical_compound ,chemistry ,Benzyl alcohol ,Polymer chemistry ,Electrochemistry ,Enantiomer ,0210 nano-technology ,Enantiomeric excess ,Selectivity ,Acetophenone - Abstract
We report new metal-free chiral electrodes for catalyzing the asymmetric reduction of aromatic ketones. Multi-walled carbon nanotubes (MWCNTs) were functionalized by chiral amino acids. The resulting amino acid-functionalized MWCNTs were fully characterized by surface analysis and spectroscopic tools and were used as a cathode for the electroreduction of 2,2,2-trifluoroacetophenone in MeCN/n-amyl alcohol (1:1)-TEAI (0.1 M). Electroreduction at l -arginine-MWCNTs and d -arginine-MWCNTs cathodes afforded, respectively, (R)- and (S)-α-(trifluoromethyl) benzyl alcohol in 60–61% yield with 43–44% enantiomeric excess (ee). The l -lysine-MWCNTs cathode gave a lower ee value of the R enantiomer (30%). The yields and ee values were a little bit lower for the electroreduction of acetophenone and other arylalkyl ketones. These amino acid-functionalized MWCNTs electrodes, in addition to showing good catalytic performance, are very stable and can be reused without loss of activity and selectivity.
- Published
- 2018
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