Specific Inhibition of the Hydrogenolysis of Benzylic C−O Bonds Using Palladium Nanoparticles Supported on Nitrogen-Doped Carbon Nanofibers

Yukihiro Motoyama, Koshi Morii, Shoya Ishizuka, Sou Inomoto, Zhenzhong Zhang, Seong Ho Yoon

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Palladium nanoparticles supported on 5 %-nitrogen-doped, herringbone-type carbon nanofibers (Pd/N-CNF-H), which are prepared by thermally decomposing [Pd2(dba)3⋅CHCl3] (dba=dibenzylideneacetone) in toluene in the presence of N-CNF-H, were found to be an efficient catalyst for the chemoselective hydrogenation of alkenyl and nitro moieties in benzyl-protected alcohols and carboxylic acid derivatives with high turnover frequencies: the hydrogenation reactions of these functional groups proceeded smoothly even at ambient temperature under atmospheric H2 pressure, and the benzyl protecting groups in the molecules remained intact. Moreover, the recovered Pd/N-CNF-H catalyst could be reused without loss of its catalytic activity or chemoselectivity. The Pd/N-CNF-H catalyst also acted as an effective hydrogenation catalyst for the reduction of aromatic ketones to the corresponding benzyl alcohol derivatives with good to high product selectivity.

Original languageEnglish
Pages (from-to)505-509
Number of pages5
JournalChemCatChem
Volume10
Issue number3
DOIs
Publication statusPublished - Feb 7 2018

Fingerprint

hydrogenolysis
Hydrogenolysis
Carbon nanofibers
Palladium
Carbon Monoxide
palladium
Nitrogen
Nanoparticles
Hydrogenation
hydrogenation
nitrogen
catalysts
nanoparticles
Catalysts
carbon
alcohols
Alcohols
Benzyl Alcohol
Derivatives
Toluene

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Specific Inhibition of the Hydrogenolysis of Benzylic C−O Bonds Using Palladium Nanoparticles Supported on Nitrogen-Doped Carbon Nanofibers. / Motoyama, Yukihiro; Morii, Koshi; Ishizuka, Shoya; Inomoto, Sou; Zhang, Zhenzhong; Yoon, Seong Ho.

In: ChemCatChem, Vol. 10, No. 3, 07.02.2018, p. 505-509.

Research output: Contribution to journalArticle

Motoyama, Yukihiro ; Morii, Koshi ; Ishizuka, Shoya ; Inomoto, Sou ; Zhang, Zhenzhong ; Yoon, Seong Ho. / Specific Inhibition of the Hydrogenolysis of Benzylic C−O Bonds Using Palladium Nanoparticles Supported on Nitrogen-Doped Carbon Nanofibers. In: ChemCatChem. 2018 ; Vol. 10, No. 3. pp. 505-509.
@article{f847bb4552aa45068d6951aa6da71ca0,
title = "Specific Inhibition of the Hydrogenolysis of Benzylic C−O Bonds Using Palladium Nanoparticles Supported on Nitrogen-Doped Carbon Nanofibers",
abstract = "Palladium nanoparticles supported on 5 {\%}-nitrogen-doped, herringbone-type carbon nanofibers (Pd/N-CNF-H), which are prepared by thermally decomposing [Pd2(dba)3⋅CHCl3] (dba=dibenzylideneacetone) in toluene in the presence of N-CNF-H, were found to be an efficient catalyst for the chemoselective hydrogenation of alkenyl and nitro moieties in benzyl-protected alcohols and carboxylic acid derivatives with high turnover frequencies: the hydrogenation reactions of these functional groups proceeded smoothly even at ambient temperature under atmospheric H2 pressure, and the benzyl protecting groups in the molecules remained intact. Moreover, the recovered Pd/N-CNF-H catalyst could be reused without loss of its catalytic activity or chemoselectivity. The Pd/N-CNF-H catalyst also acted as an effective hydrogenation catalyst for the reduction of aromatic ketones to the corresponding benzyl alcohol derivatives with good to high product selectivity.",
author = "Yukihiro Motoyama and Koshi Morii and Shoya Ishizuka and Sou Inomoto and Zhenzhong Zhang and Yoon, {Seong Ho}",
year = "2018",
month = "2",
day = "7",
doi = "10.1002/cctc.201701326",
language = "English",
volume = "10",
pages = "505--509",
journal = "ChemCatChem",
issn = "1867-3880",
publisher = "Wiley - VCH Verlag GmbH & CO. KGaA",
number = "3",

}

TY - JOUR

T1 - Specific Inhibition of the Hydrogenolysis of Benzylic C−O Bonds Using Palladium Nanoparticles Supported on Nitrogen-Doped Carbon Nanofibers

AU - Motoyama, Yukihiro

AU - Morii, Koshi

AU - Ishizuka, Shoya

AU - Inomoto, Sou

AU - Zhang, Zhenzhong

AU - Yoon, Seong Ho

PY - 2018/2/7

Y1 - 2018/2/7

N2 - Palladium nanoparticles supported on 5 %-nitrogen-doped, herringbone-type carbon nanofibers (Pd/N-CNF-H), which are prepared by thermally decomposing [Pd2(dba)3⋅CHCl3] (dba=dibenzylideneacetone) in toluene in the presence of N-CNF-H, were found to be an efficient catalyst for the chemoselective hydrogenation of alkenyl and nitro moieties in benzyl-protected alcohols and carboxylic acid derivatives with high turnover frequencies: the hydrogenation reactions of these functional groups proceeded smoothly even at ambient temperature under atmospheric H2 pressure, and the benzyl protecting groups in the molecules remained intact. Moreover, the recovered Pd/N-CNF-H catalyst could be reused without loss of its catalytic activity or chemoselectivity. The Pd/N-CNF-H catalyst also acted as an effective hydrogenation catalyst for the reduction of aromatic ketones to the corresponding benzyl alcohol derivatives with good to high product selectivity.

AB - Palladium nanoparticles supported on 5 %-nitrogen-doped, herringbone-type carbon nanofibers (Pd/N-CNF-H), which are prepared by thermally decomposing [Pd2(dba)3⋅CHCl3] (dba=dibenzylideneacetone) in toluene in the presence of N-CNF-H, were found to be an efficient catalyst for the chemoselective hydrogenation of alkenyl and nitro moieties in benzyl-protected alcohols and carboxylic acid derivatives with high turnover frequencies: the hydrogenation reactions of these functional groups proceeded smoothly even at ambient temperature under atmospheric H2 pressure, and the benzyl protecting groups in the molecules remained intact. Moreover, the recovered Pd/N-CNF-H catalyst could be reused without loss of its catalytic activity or chemoselectivity. The Pd/N-CNF-H catalyst also acted as an effective hydrogenation catalyst for the reduction of aromatic ketones to the corresponding benzyl alcohol derivatives with good to high product selectivity.

UR - http://www.scopus.com/inward/record.url?scp=85041793784&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85041793784&partnerID=8YFLogxK

U2 - 10.1002/cctc.201701326

DO - 10.1002/cctc.201701326

M3 - Article

AN - SCOPUS:85041793784

VL - 10

SP - 505

EP - 509

JO - ChemCatChem

JF - ChemCatChem

SN - 1867-3880

IS - 3

ER -