Ionic TEMPO in Ionic Liquids: Specific Promotion of the Aerobic Oxidation of Alcohols

Tsunehisa Hirashita; Makoto Nakanishi; Tomoya Uchida; Masakazu Yamamoto; Shuki Araki; Isabel W C E Arends; Roger A. Sheldon

doi:10.1002/cctc.201600491

Ionic TEMPO in Ionic Liquids: Specific Promotion of the Aerobic Oxidation of Alcohols

Tsunehisa Hirashita^*, Makoto Nakanishi, Tomoya Uchida, Masakazu Yamamoto, Shuki Araki, Isabel W C E Arends, Roger A. Sheldon

^*Corresponding author for this work

Research output: Contribution to journal › Article › Scientific › peer-review

17 Citations (Scopus)

Abstract

The main objective of this study was to design a recyclable TEMPO (2,2,6,6-tetramethylpiperidinyl-N-oxyl) derivative that could be used as a catalyst in an ionic liquid solvent for the aerobic oxidation of alcohols by using NaNO₂ and HCl as co-catalysts. To this end, a TEMPO derivative bearing a quaternary ammonium group, [4-Bu₂MeN-TEMPO][PF₆] (1), was prepared. It was subsequently shown that this ionic TEMPO derivative is an efficient catalyst for the aerobic oxidation of a variety of primary and secondary alcohols. It exhibits a synergistic effect with ionic liquid solvents and readily outperforms analogous oxidations in methylene chloride. Moreover, the ionic TEMPO could be recycled five times with no loss of activity.

Original language	English
Pages (from-to)	2704-2709
Number of pages	6
Journal	ChemCatChem
Volume	8
Issue number	16
DOIs	https://doi.org/10.1002/cctc.201600491
Publication status	Published - 22 Aug 2016

Keywords

alcohols
ionic liquids
oxidation
oxygen
radicals

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10.1002/cctc.201600491

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abstract = "The main objective of this study was to design a recyclable TEMPO (2,2,6,6-tetramethylpiperidinyl-N-oxyl) derivative that could be used as a catalyst in an ionic liquid solvent for the aerobic oxidation of alcohols by using NaNO2 and HCl as co-catalysts. To this end, a TEMPO derivative bearing a quaternary ammonium group, [4-Bu2MeN-TEMPO][PF6] (1), was prepared. It was subsequently shown that this ionic TEMPO derivative is an efficient catalyst for the aerobic oxidation of a variety of primary and secondary alcohols. It exhibits a synergistic effect with ionic liquid solvents and readily outperforms analogous oxidations in methylene chloride. Moreover, the ionic TEMPO could be recycled five times with no loss of activity.",

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T2 - Specific Promotion of the Aerobic Oxidation of Alcohols

AU - Hirashita, Tsunehisa

AU - Nakanishi, Makoto

AU - Uchida, Tomoya

AU - Yamamoto, Masakazu

AU - Araki, Shuki

AU - Arends, Isabel W C E

AU - Sheldon, Roger A.

PY - 2016/8/22

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AB - The main objective of this study was to design a recyclable TEMPO (2,2,6,6-tetramethylpiperidinyl-N-oxyl) derivative that could be used as a catalyst in an ionic liquid solvent for the aerobic oxidation of alcohols by using NaNO2 and HCl as co-catalysts. To this end, a TEMPO derivative bearing a quaternary ammonium group, [4-Bu2MeN-TEMPO][PF6] (1), was prepared. It was subsequently shown that this ionic TEMPO derivative is an efficient catalyst for the aerobic oxidation of a variety of primary and secondary alcohols. It exhibits a synergistic effect with ionic liquid solvents and readily outperforms analogous oxidations in methylene chloride. Moreover, the ionic TEMPO could be recycled five times with no loss of activity.

KW - alcohols

KW - ionic liquids

KW - oxidation

KW - oxygen

KW - radicals

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JF - ChemCatChem

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ER -

Ionic TEMPO in Ionic Liquids: Specific Promotion of the Aerobic Oxidation of Alcohols

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Keywords

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