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Synfacts 2015; 11(8): 0879
DOI: 10.1055/s-0034-1381113
DOI: 10.1055/s-0034-1381113
Polymer-Supported Synthesis
Enantioselective Hydrogenation of Ketones on Palladium/Cellulose Nanocrystals
Kaushik M, Basu K, Benoit C, Cirtiu CM, Vali H, Moores A * McGill University, Montréal and Institut National de Santé Publique du Québec, Quebec City, Canada
Cellulose Nanocrystals as Chiral Inducers: Enantioselective Catalysis and Transmission Electron Microscopy 3D Characterization.
J. Am. Chem. Soc. 2015;
137: 6124-6127
Cellulose Nanocrystals as Chiral Inducers: Enantioselective Catalysis and Transmission Electron Microscopy 3D Characterization.
J. Am. Chem. Soc. 2015;
137: 6124-6127
Further Information
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.
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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.
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