Iodoxybenzoic Acid Supported on Multi Walled Carbon Nanotubes as Biomimetic Environmental Friendly Oxidative Systems for the Oxidation of Alcohols to Aldehydes.

Bruno Mattia Bizzarri,Lorenzo Botta,Anna Rita Taddei,Stefano Nisi,Raffaele Saladino,Maurizio Passacantando,Issam Abdalghani,Marcello Crucianelli,Marco Ferrante

doi:10.3390/nano8070516

Bruno Mattia Bizzarri, Lorenzo Botta + Show 7 more

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https://doi.org/10.3390/nano8070516

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Abstract

Iodoxybenzoic acid (IBX) supported multi walled carbon nanotube (MWCNT) derivatives have been prepared as easily recyclable solid reagents. These compounds have been shown to be able to mimic the alcohol dehydrogenases and monooxygenases promoted oxidation of aromatic alcohols to corresponding aldehydes. Their reactivity was found to be dependent on the degree of functionalization of MWCNTs as well as from the chemical properties of the spacers used to bind IBX on the surface of the support. Au-decorated MWCNTs and the presence of longer spacers resulted in the optimal experimental conditions. A high conversion of the substrates and yield of desired products were obtained.

Highlights

The oxidation of alcohols to corresponding carbonyl compounds is one of the most fundamental and important processes in synthetic organic chemistry
The preparation of a series of IBX based reagents supported on multi walled carbon nanotube (MWCNT), as heterogeneous biomimetic systems for the selective oxidation of primary alcohols to the corresponding aldehydes under mild conditions, has been described
The immobilization of the iodine active reagent was realized by exploiting the direct formation of an amide linkage with IBX, mediated by different spacer lengths, or through the high binding affinity of sulfur containing linkers in the case of the Au-decorated MWCNTs

Summary

Introduction

The oxidation of alcohols to corresponding carbonyl compounds is one of the most fundamental and important processes in synthetic organic chemistry. Metal-free oxidations are desired processes in the context of green-chemistry due to the known toxicity and high environmental impact of metal species. In this context, biotechnological applications of oxidative enzymes, e.g., alcohol dehydrogenases and monooxygenases with high environmental compatibility, have been widely evaluated [7]. Continuous interest is devoted to developing biomimetic and environmentally friendly metal-free solid supported reagents for the selective oxidation of alcohols that are able to mimic a biological material in its structure or function [11]

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