TY - JOUR
T1 - Development of Carbon-Neutral Cellulose-Supported Heterogeneous Palladium Catalysts for Chemoselective Hydrogenation
AU - Yamada, Tsuyoshi
AU - Teranishi, Wataru
AU - Park, Kwihwan
AU - Jiang, Jing
AU - Tachikawa, Takumu
AU - Furusato, Shinichi
AU - Sajiki, Hironao
N1 - Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2020/8/20
Y1 - 2020/8/20
N2 - 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.
AB - 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.
KW - Carbon-neutral support
KW - Cellulose
KW - Chemoselective hydrogenation
KW - Continuous-flow reaction
KW - Heterogeneous catalyst
UR - http://www.scopus.com/inward/record.url?scp=85087674108&partnerID=8YFLogxK
U2 - 10.1002/cctc.202000805
DO - 10.1002/cctc.202000805
M3 - 学術論文
AN - SCOPUS:85087674108
SN - 1867-3880
VL - 12
SP - 4052
EP - 4058
JO - ChemCatChem
JF - ChemCatChem
IS - 16
ER -