Fullerene as a Platform for Recyclable TEMPO Organocatalysts for the Oxidation of Alcohols

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Abstract

[60]Fullerene has been employed successfully as a molecular platform to anchor 12 2,2,6,6-tetramethylpiperidine-1-oxyl(TEMPO) moieties. Such an octahedrally substituted C60-derivative has been employed as an organocatalyst for the oxidation of primary and secondary alcohols using the Anelli protocol. The reaction showed a general applicability to various alcohols, and the catalyst was recovered easily and could be recycled for at least seven cycles with no loss in catalytic activity. EPR spectroscopy studies revealed that the amount of radicals decreases during the catalytic cycles, even if the recovered material still displays unchanged catalytic activity. This new approach paves the way to use fullerene as a molecular platform to support other kinds of organometallic and organocatalysts as well as for their use as model compounds to understand the behavior of other nanocarbon-supported catalysts.
Lingua originaleEnglish
pagine (da-a)2419-2424
Numero di pagine6
RivistaChemCatChem
Volume6
Stato di pubblicazionePublished - 2014

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Fullerenes
fullerenes
catalytic activity
Catalyst activity
alcohols
Alcohols
platforms
catalysts
Oxidation
oxidation
cycles
Organometallics
Anchors
Catalyst supports
Paramagnetic resonance
Spectroscopy
Catalysts
spectroscopy
TEMPO
fullerene C60

All Science Journal Classification (ASJC) codes

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

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title = "Fullerene as a Platform for Recyclable TEMPO Organocatalysts for the Oxidation of Alcohols",
abstract = "[60]Fullerene has been employed successfully as a molecular platform to anchor 12 2,2,6,6-tetramethylpiperidine-1-oxyl(TEMPO) moieties. Such an octahedrally substituted C60-derivative has been employed as an organocatalyst for the oxidation of primary and secondary alcohols using the Anelli protocol. The reaction showed a general applicability to various alcohols, and the catalyst was recovered easily and could be recycled for at least seven cycles with no loss in catalytic activity. EPR spectroscopy studies revealed that the amount of radicals decreases during the catalytic cycles, even if the recovered material still displays unchanged catalytic activity. This new approach paves the way to use fullerene as a molecular platform to support other kinds of organometallic and organocatalysts as well as for their use as model compounds to understand the behavior of other nanocarbon-supported catalysts.",
author = "Michelangelo Gruttadauria and Francesco Giacalone and Beejapur, {Hazi Ahmad} and Vincenzo Campisciano and Marco Lucarini and Paola Franchi",
year = "2014",
language = "English",
volume = "6",
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T1 - Fullerene as a Platform for Recyclable TEMPO Organocatalysts for the Oxidation of Alcohols

AU - Gruttadauria, Michelangelo

AU - Giacalone, Francesco

AU - Beejapur, Hazi Ahmad

AU - Campisciano, Vincenzo

AU - Lucarini, Marco

AU - Franchi, Paola

PY - 2014

Y1 - 2014

N2 - [60]Fullerene has been employed successfully as a molecular platform to anchor 12 2,2,6,6-tetramethylpiperidine-1-oxyl(TEMPO) moieties. Such an octahedrally substituted C60-derivative has been employed as an organocatalyst for the oxidation of primary and secondary alcohols using the Anelli protocol. The reaction showed a general applicability to various alcohols, and the catalyst was recovered easily and could be recycled for at least seven cycles with no loss in catalytic activity. EPR spectroscopy studies revealed that the amount of radicals decreases during the catalytic cycles, even if the recovered material still displays unchanged catalytic activity. This new approach paves the way to use fullerene as a molecular platform to support other kinds of organometallic and organocatalysts as well as for their use as model compounds to understand the behavior of other nanocarbon-supported catalysts.

AB - [60]Fullerene has been employed successfully as a molecular platform to anchor 12 2,2,6,6-tetramethylpiperidine-1-oxyl(TEMPO) moieties. Such an octahedrally substituted C60-derivative has been employed as an organocatalyst for the oxidation of primary and secondary alcohols using the Anelli protocol. The reaction showed a general applicability to various alcohols, and the catalyst was recovered easily and could be recycled for at least seven cycles with no loss in catalytic activity. EPR spectroscopy studies revealed that the amount of radicals decreases during the catalytic cycles, even if the recovered material still displays unchanged catalytic activity. This new approach paves the way to use fullerene as a molecular platform to support other kinds of organometallic and organocatalysts as well as for their use as model compounds to understand the behavior of other nanocarbon-supported catalysts.

UR - http://hdl.handle.net/10447/96164

UR - http://onlinelibrary.wiley.com/doi/10.1002/cctc.201402262/abstract

M3 - Article

VL - 6

SP - 2419

EP - 2424

JO - ChemCatChem

JF - ChemCatChem

SN - 1867-3880

ER -