Development of Carbon‐Neutral Cellulose‐Supported Heterogeneous Palladium Catalysts for Chemoselective Hydrogenation

Palladium catalysts immobilized on cellulose particles (Pd/CLP) and on a cellulose‐monolith (Pd/CLM) were developed. These composites were applied as hydrogenation catalysts and their catalyst activities were evaluated. Although both catalysts catalyzed the deprotection of benzyloxycarbonyl‐protecte...

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Bibliographic Details
Published in:ChemCatChem 2020-08, Vol.12 (16), p.4052-4058
Main Authors: Yamada, Tsuyoshi, Teranishi, Wataru, Park, Kwihwan, Jiang, Jing, Tachikawa, Takumu, Furusato, Shinichi, Sajiki, Hironao
Format: Article
Language:English
Subjects:
Aliphatic compounds
Alkynes
Amines
Carbon-neutral support
Catalysts
Cellulose
Chemoselective hydrogenation
Continuous-flow reaction
Esters
Heterogeneous catalyst
Hydrogenation
Hydrogenolysis
Oxidation
Palladium
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Summary:Palladium catalysts immobilized on cellulose particles (Pd/CLP) and on a cellulose‐monolith (Pd/CLM) were developed. These composites were applied as hydrogenation catalysts and their catalyst activities were evaluated. Although both catalysts catalyzed the deprotection of benzyloxycarbonyl‐protected aromatic amines (Ar‐N‐Cbz) and aromatic benzyl esters (Ar‐CO2Bn), only Pd/CLM could accomplish the hydrogenolysis of aliphatic‐N‐Cbz and aliphatic‐CO2Bn protective groups. The difference in the physical structure of the cellulose supports induced unique chemoselectivity. Aliphatic‐N‐Cbz and aliphatic‐CO2Bn groups were tolerated under the Pd/CLP‐catalyzed hydrogenation conditions, while Ar‐N‐Cbz, Ar‐CO2Bn, alkene, alkyne, azido and nitro groups could be smoothly reduced. Chemoselective hydrogenation in flask and flow: Newly developed palladium catalysts immobilized on cellulose particle (Pd/CLP), and cellulose‐monolith (Pd/CLM) efficiently catalyzed chemoselective hydrogenation of various reducible functionalities including deprotection of an aromatic N‐benzyloxycarbonyl protective group. Although limited to Pd/CLM, the hydrogenolysis of an aliphatic‐N‐Cbz protective group could also accomplish, and it was applicable to continuous‐flow hydrogenation reactions.
ISSN:1867-3880
1867-3899
DOI:10.1002/cctc.202000805