Abstract
The oxidation of alcohols to the corresponding carbonyl products is an important organic transformation and the products are used in a variety of applications. The development of catalytic methods for selective alcohol oxidation have garnered significant attention in an attempt to find a more sustainable method without any limitations. Copper, in combination with 2,2,6,6-tetramethyl-1-piperidine N-oxyl (TEMPO) and supported by organic ligands, have emerged as the most effective catalysts for selective alcohol oxidation and these catalyst systems are frequently compared to galactose oxidase (GOase). The efficiency of GOase has led to extensive research to mimic the active sites of these enzymes, leading to a variety of Cu/TEMPO· catalyst systems being reported over the years. The mechanistic pathway by which Cu/TEMPO· catalyst systems operate has been investigated by several research groups, which led to partially contradicting mechanistic description. Due to the disadvantages and limitations of employing TEMPO· as co-catalyst, alternative nitroxyl radicals or in situ formed radicals, as co-catalysts, have been successfully evaluated in alcohol oxidation. Herein we discuss the development and mechanistic elucidation of Cu/TEMPO· catalyst systems as biomimetic alcohol oxidation catalysts.
Highlights
Aldehydes and ketones are important intermediates in the pharmaceutical industry [1,2] as well as for the synthesis of fine chemicals such as fragrances and food additives [3]
This review sought to highlight the importance of copper as a metal, as well as in combination with tetramethyl-1-piperidine N-oxyl (TEMPO)·, for alcohol oxidation reactions
The advantages, disadvantages and differences associated with the reported Cu/TEMPO· catalyst systems have been summarised, while the potential for new developments, such as a catalyst system for optimal oxidation of both primary and secondary
Summary
Aldehydes and ketones are important intermediates in the pharmaceutical industry [1,2] as well as for the synthesis of fine chemicals such as fragrances and food additives [3]. A number of reviews catalytic copper oxidation chemistry have appeared, with focus withspecifically a range of on oxidants such as oxygen, as well as possible mechanistic pathways for selective reaction the application of Cu‐based catalyst systems in the aerobic functionalisation of C‐H types [13,14,15,16]. Catalyst systems for alcohol oxidation, combination a range of oxidants as oxygen, as well as possible mechanistic pathways for up toselective. 2018, the different partially contradicting mechanistic pathways proposed for Catalyst this metal, as well as in combination with TEMPO·, for alcohol oxidation reactions are described. TEMPO·, for alcohol oxidation proposed mechanistic pathways for alcohol oxidation, are discussed in detail, with particular emphasis reactions are described. The different proposed mechanistic pathways for alcohol oxidation, are discussed are described. Recent advances in the development of alternative co‐catalysts are described
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