Oxidation of secondary alcohols using solid-supported hypervalent iodine catalysts

Ballaschk, Frederic; Kirsch, Stefan F.

doi:10.1039/c9gc02605c

Cited by 25 publications

(21 citation statements)

References 81 publications

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“…91 Polymer-supported hypervalent iodine pre-catalysts 89 and 90 were synthesised by Kirsch and Ballaschk and revealed their potential application in the oxidation of secondary alcohols 81 to corresponding ketones 82 (Scheme 23). 93 The primacy of this green synthesis is the multiple reusability of the catalyst without losing much catalytic activity and easy work-up. A wide range of secondary alcohols including cyclic, bicyclic and benzylic alcohols were tolerated.…”

Section: Oxidation Reactionsmentioning

confidence: 99%

Progress in organocatalysis with hypervalent iodine catalysts

et al. 2022

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Section: Oxidation Reactionsmentioning

confidence: 99%

Progress in organocatalysis with hypervalent iodine catalysts

et al. 2022

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“…In 2019, Kirsch and Ballaschk synthesized solid-supported hypervalent iodine (V) catalysts (50, 51) derived from IBX and IBS derivatives for the oxidation of secondary alcohols (Figure 2). 59 Treatment of secondary alcohols with hypervalent iodine (V) (5 mol %) and oxone as co-oxidant resulted in the formation of ketones upto 98% yield. IBS-derived catalyst 51 showed superior reactivity over 50 and requires less reaction time as compared to 50.…”

Section: Dimerization Of Alkenesmentioning

confidence: 99%

Hypervalent iodine (V) catalyzed reactions

Kumar¹,

Soni²,

Rimi³

et al. 2022

Arkivoc

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The chemistry of hypervalent iodine compounds has been widely recognized in the synthetic community. The utilization of hypervalent iodine compounds as stoichiometric reagents as well as catalysts has tremendously been studied in recent decades. Hypervalent iodine (V)-catalyzed reactions are proven to be versatile catalytic systems to access various oxidative transformations. In this review, the versatility of hypervalent iodine (V)catalyzed reactions have been discussed in detail. This review highlights the oxidation of various substrates using catalytic amounts of o-iodoxybenzoic acid (IBX), modified IBX derivatives, o-iodoxybenzenesulfonic acid (IBS), recyclable iodine (V), and non-cyclic/pseudocyclic iodine (V) compounds.

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“…Iodine is used in several degrees of oxidation and depending on the conditions helps to regulate its oxidizing power. For example, hypervalent iodine derivatives are known for the selective oxidation of primary alcohols into aldehydes [158,159] particularly 2-iodoxybenzenesulfonic acid (IBS). [160] We have been able to demonstrate the effectiveness of this catalyst in selectively converting HMF into DFF.…”

Section: Organic Catalystsmentioning

confidence: 99%

Metal vs. Metal‐Free Catalysts for Oxidation of 5‐Hydroxymethylfurfural and Levoglucosenone to Biosourced Chemicals

et al. 2022

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Lignocellulosic feedstocks, such as forestry biomass and agricultural crop residues, can be utilized to generate biofuels and biochemicals. Converting these organic waste materials into biochemicals is widely regarded as a remedial approach to develop a sustainable, clean, and green energy source. Nevertheless, are these methods sustainable and clean? Prior studies have shown that most such conversions use metals -including heavy metals or noble metals -as catalysts. In addition to the fact that many metals (e. g., aluminum, cobalt, titanium, platinum) have been listed as critical minerals, these methods suffer from high cost, deactivation, and leakage problems and the release of toxic wastes. This Review summarizes catalytic methods using metal and metal-free catalysts for the oxidation of the platform molecules 5-hydroxymethylfurfural and levoglucosenone and demonstrates the potential and effectiveness of metal-free catalysts.

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Oxidation of secondary alcohols using solid-supported hypervalent iodine catalysts

Abstract: Solid-supported catalysts for the oxidation of secondary alcohols are disclosed, featuring metal-free conditions, low catalyst loadings and easy reusability.

Cited by 25 publications

References 81 publications

Progress in organocatalysis with hypervalent iodine catalysts

Progress in organocatalysis with hypervalent iodine catalysts

Hypervalent iodine (V) catalyzed reactions

Metal vs. Metal‐Free Catalysts for Oxidation of 5‐Hydroxymethylfurfural and Levoglucosenone to Biosourced Chemicals

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