Sol-gel immobilized aryl iodides for the catalytic oxidative α-tosyloxylation of ketones

Wusheng Guo; Amàlia Monge-Marcet; Xavier Cattoën; Alexandr Shafir; Roser Pleixats

doi:10.1016/j.reactfunctpolym.2012.10.011

Sol-gel immobilized aryl iodides for the catalytic oxidative α-tosyloxylation of ketones

Wusheng Guo, Amàlia Monge-Marcet, Xavier Cattoën, Alexandr Shafir, Roser Pleixats

Department of Chemistry

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

9 Citations (Scopus)

Abstract

New hybrid silica materials M1-M4, derived from mono and bis-silylated aryl iodides, have been prepared via sol-gel processes, either by the hydrolytic polycondensation of a bis-silylated monomer or by the co-gelification of a monosilylated precursor with tetraethylorthosilicate. They have been fully characterized by elemental analysis, 13C and 29Si CP-MAS solid state NMR, IR, TGA, and nitrogen-sorption measurements. These organosilicas have been successfully applied as supported catalysts in the α-tosyloxylation of aliphatic ketones in the presence of m-chloroperbenzoic acid (m-CPBA) as an oxidant, with the corresponding α-tosyloxyketones obtained in moderate to good isolated yields. The recyclability of the supported catalysts by a simple filtration has also been investigated. © 2012 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	192-199
Journal	Reactive and Functional Polymers
Volume	73
Issue number	1
DOIs	https://doi.org/10.1016/j.reactfunctpolym.2012.10.011
Publication status	Published - 1 Jan 2013

Keywords

Hybrid silica
Hypervalent iodine
Oxidative α-tosyloxylation
Recyclable catalyst
Sol-gel

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title = "Sol-gel immobilized aryl iodides for the catalytic oxidative α-tosyloxylation of ketones",

abstract = "New hybrid silica materials M1-M4, derived from mono and bis-silylated aryl iodides, have been prepared via sol-gel processes, either by the hydrolytic polycondensation of a bis-silylated monomer or by the co-gelification of a monosilylated precursor with tetraethylorthosilicate. They have been fully characterized by elemental analysis, 13C and 29Si CP-MAS solid state NMR, IR, TGA, and nitrogen-sorption measurements. These organosilicas have been successfully applied as supported catalysts in the α-tosyloxylation of aliphatic ketones in the presence of m-chloroperbenzoic acid (m-CPBA) as an oxidant, with the corresponding α-tosyloxyketones obtained in moderate to good isolated yields. The recyclability of the supported catalysts by a simple filtration has also been investigated. {\textcopyright} 2012 Elsevier Ltd. All rights reserved.",

keywords = "Hybrid silica, Hypervalent iodine, Oxidative α-tosyloxylation, Recyclable catalyst, Sol-gel",

author = "Wusheng Guo and Am{\`a}lia Monge-Marcet and Xavier Catto{\"e}n and Alexandr Shafir and Roser Pleixats",

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T1 - Sol-gel immobilized aryl iodides for the catalytic oxidative α-tosyloxylation of ketones

AU - Guo, Wusheng

AU - Monge-Marcet, Amàlia

AU - Cattoën, Xavier

AU - Shafir, Alexandr

AU - Pleixats, Roser

PY - 2013/1/1

Y1 - 2013/1/1

N2 - New hybrid silica materials M1-M4, derived from mono and bis-silylated aryl iodides, have been prepared via sol-gel processes, either by the hydrolytic polycondensation of a bis-silylated monomer or by the co-gelification of a monosilylated precursor with tetraethylorthosilicate. They have been fully characterized by elemental analysis, 13C and 29Si CP-MAS solid state NMR, IR, TGA, and nitrogen-sorption measurements. These organosilicas have been successfully applied as supported catalysts in the α-tosyloxylation of aliphatic ketones in the presence of m-chloroperbenzoic acid (m-CPBA) as an oxidant, with the corresponding α-tosyloxyketones obtained in moderate to good isolated yields. The recyclability of the supported catalysts by a simple filtration has also been investigated. © 2012 Elsevier Ltd. All rights reserved.

AB - New hybrid silica materials M1-M4, derived from mono and bis-silylated aryl iodides, have been prepared via sol-gel processes, either by the hydrolytic polycondensation of a bis-silylated monomer or by the co-gelification of a monosilylated precursor with tetraethylorthosilicate. They have been fully characterized by elemental analysis, 13C and 29Si CP-MAS solid state NMR, IR, TGA, and nitrogen-sorption measurements. These organosilicas have been successfully applied as supported catalysts in the α-tosyloxylation of aliphatic ketones in the presence of m-chloroperbenzoic acid (m-CPBA) as an oxidant, with the corresponding α-tosyloxyketones obtained in moderate to good isolated yields. The recyclability of the supported catalysts by a simple filtration has also been investigated. © 2012 Elsevier Ltd. All rights reserved.

KW - Hybrid silica

KW - Hypervalent iodine

KW - Oxidative α-tosyloxylation

KW - Recyclable catalyst

KW - Sol-gel

U2 - 10.1016/j.reactfunctpolym.2012.10.011

DO - 10.1016/j.reactfunctpolym.2012.10.011

M3 - Article

VL - 73

SP - 192

EP - 199

JO - Reactive and Functional Polymers

JF - Reactive and Functional Polymers

SN - 1381-5148

IS - 1

ER -