Optimised Conditions for the Palladium-Catalyzed Hydrogenolysis of Benzyl and Naphthylmethyl Ethers: Preventing Saturation of Aromatic Protecting Groups

26 March 2020, Version 2
This content is a preprint and has not undergone peer review at the time of posting.


Whilst carrying out palladium catalysed hydrogenolysis to deprotect synthetic oligosaccharides, saturation of the benzyl and naphthylmethyl ether groups to their corresponding ether was observed. In order to suppress this unwanted hydrogenation, we report a scalable practical approach using a catalyst pre-treatment strategy, which is effective under batch or continuous flow conditions. This suppressed the unwanted hydrogenation side-products and created a selective catalyst for hydrogenolysis of benzyl and naphthylmethyl ethers. We demonstrate the efficient deprotection of a set of structurally diverse oligosaccharides (5 examples, >73%).


Carbohydrate Chemistry
hydrogenolysis transformations


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