Facile Cleavage of Benzyl Ethers by Catalytic Transfer Hydrogenation

Synthesis ◽  
1981 ◽  
Vol 1981 (05) ◽  
pp. 396-397 ◽  
Author(s):  
Stephen Hanessian ◽  
Teng Jiam Liak ◽  
Benoit Vanasse
Keyword(s):  
Transfer Hydrogenation ◽  
Catalytic Transfer Hydrogenation ◽  
Benzyl Ethers ◽  
Catalytic Transfer

scholarly journals Removal of benzylidene acetal and benzyl ether in carbohydrate derivatives using triethylsilane and Pd/C

2013 ◽  
Vol 9 ◽  
pp. 74-78 ◽  
Author(s):  
Abhishek Santra ◽  
Tamashree Ghosh ◽  
Anup Kumar Misra
Keyword(s):  
Room Temperature ◽  
Transfer Hydrogenation ◽  
Benzyl Ether ◽  
Catalytic Transfer Hydrogenation ◽  
Excellent Yield ◽  
Benzyl Ethers ◽  
Catalytic Transfer

Clean deprotection of carbohydrate derivatives containing benzylidene acetals and benzyl ethers was achieved under catalytic transfer hydrogenation conditions by using a combination of triethylsilane and 10% Pd/C in CH3OH at room temperature. A variety of carbohydrate diol derivatives were prepared from their benzylidene derivatives in excellent yield.

Catalytic transfer hydrogenation of benzylic and styryl compounds with palladium/carbon and 2-propanol. Selective removal of O-benzyl groups from carbohydrate derivatives

1983 ◽  
Vol 61 (4) ◽  
pp. 652-657 ◽  
Author(s):  
Vanga S. Rao ◽  
Arthur S. Perlin
Keyword(s):  
Phenyl Group ◽  
Hydrogen Donor ◽  
Transfer Hydrogenation ◽  
Catalytic Transfer Hydrogenation ◽  
Benzyl Ethers ◽  
Hydrogenation Reactions ◽  
Catalytic Transfer ◽  
Anchoring Group ◽  
Supported Palladium ◽  
Derivatives Of

2-Propanol is shown to be an effective hydrogen donor, in the presence of palladium/carbon, for catalytic transfer hydrogenation reactions of benzylic and styryl compounds, e.g., for the quantitative conversion of cinnamyl alcohol into 3-phenylpropanol. In the reduction of derivatives of cinnamic acid, decarboxylation also occurs. During the latter reaction, the phenyl group appears to function as an anchoring group for the palladium atom, because derivatives of phenylpropanoic acid are decarboxylated more readily than are those of phenylacetic acid. In hydrogenolysis reactions, aryl alcohols undergo disporportionation whereas benzyl ethers, represented by O-benzyl and related derivatives of carbohydrates, are smoothly cleaved. Although 2-propanol is less reactive as a hydrogen donor than formic acid, it exhibits greater selectivity, as illustrated by relative rates of hydrogenolysis of O-benzyl and O-benzylidene substituents. The use of alumina-supported palladium is more effective than palladium/carbon for promoting stepwise removal of O-benzyl substituents, as shown by the preparation of methyl 2-O-benzyl- and -3-O-benzyl-α-D-glucopyranoside from the 2,3-di-O-benzyl derivative. A possible relationship between the orientation of O-benzyl groups and the chemical shift differences between the diastereotopic benzylic protons is described.

Ruthenium (ii) complexes with c- and c-symmetric bis-(+)-camphopyrazole ligands and their evaluation in catalytic transfer hydrogenation of aldehydes

2021 ◽  
pp. 120429
Author(s):  
Christian O. Blanco ◽  
Ligia Llovera ◽  
Alberto Herrera ◽  
Romano Dorta ◽  
Giuseppe Agrifoglio ◽  
...  
Keyword(s):  
Transfer Hydrogenation ◽  
Catalytic Transfer Hydrogenation ◽  
Catalytic Transfer
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