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DOI: 10.1055/s-0034-1381113
Enantioselective Hydrogenation of Ketones on Palladium/Cellulose Nanocrystals
Cellulose Nanocrystals as Chiral Inducers: Enantioselective Catalysis and Transmission Electron Microscopy 3D Characterization.
J. Am. Chem. Soc. 2015;
137: 6124-6127
Publication History
Publication Date:
20 July 2015 (online)
Significance
Palladium(0) deposited on cellulose nanocrystals (Pd@CNCs) was prepared by treatment of CNCs with palladium(II) chloride in aqueous hydrochloric acid, followed by the reduction with hydrogen gas. The Pd@CNCs was used in an enantioselective hydrogenation of prochiral ketones under hydrogen pressure in water to give the corresponding alcohols in 67–91% yield and 5–65% ee.
Comment
The aqueous suspension of Pd@CNCs was reused twice without significant loss of the catalytic activity or enantioselectivity. CSCs did not catalyze the carbonyl hydrogenation in the absence of palladium. Hydrogenation of 2-methoxyacetophenone on PdNPs@C under similar conditions gave the corresponding racemic alcohol in 38% yield.