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Development of Carbon‐Neutral Cellulose‐Supported Heterogeneous Palladium Catalysts for Chemoselective Hydrogenation
Author(s) -
Yamada Tsuyoshi,
Teranishi Wataru,
Park Kwihwan,
Jiang Jing,
Tachikawa Takumu,
Furusato Shinichi,
Sajiki Hironao
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202000805
Subject(s) - hydrogenolysis , chemoselectivity , catalysis , cellulose , alkene , chemistry , alkyne , palladium , organic chemistry , heterogeneous catalysis , nitro , polymer chemistry , alkyl
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‐CO 2 Bn), only Pd/CLM could accomplish the hydrogenolysis of aliphatic‐ N‐ Cbz and aliphatic‐CO 2 Bn protective groups. The difference in the physical structure of the cellulose supports induced unique chemoselectivity. Aliphatic‐ N‐ Cbz and aliphatic‐CO 2 Bn groups were tolerated under the Pd/CLP‐catalyzed hydrogenation conditions, while Ar‐ N‐ Cbz, Ar‐CO 2 Bn, alkene, alkyne, azido and nitro groups could be smoothly reduced.