Potassium 4-Iodylbenzenesulfonate (PIBS): An Efficient Recyclable Hypervalent Iodine Reagent for Iodo-functionalization of Alkenes, Alkynes and Ketones

Mironova, Irina A.; Yusubova, Rosa Y.; Kukurina, Olga; Yusubov, Mekhman S.; Zhdankin, Viktor V.

doi:10.2174/1570179413666151218204056

Cited by 3 publications

(7 citation statements)

References 49 publications

(59 reference statements)

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“…93 Zhdankin et al also reported the synthesis of the recyclable and water-soluble I(V) reagent potassium 4-iodylbenzenesulfonate (PIBS) (204) via the oxidation of 4-iodobenzenesulfonic acid using Oxone ® in water. 94 This watersoluble reagent can be used for the oxidative iodination of arenes, 94 alkenes, 95 alkynes, 95 and ketones 95 (Scheme 40). Unreacted PIBS (204) and its reduced form PIBS-H can be recovered from the reaction mixture.…”

Section: Recyclable Non-polymeric Hypervalent Iodine(v) Reagentsmentioning

confidence: 99%

“…Unreacted PIBS ( 204 ) and its reduced form PIBS-H can be recovered from the reaction mixture. 94 95…”

Section: Non-polymeric Recyclable Hypervalent Iodine Reagentsmentioning

confidence: 99%

“…To overcome this limitation, various recyclable HVI(V) reagents have been reported in the literature. 90 91 92 93 94 95 96 97 98 99 The structures of these reagents are shown in Figure 10 .…”

Section: Non-polymeric Recyclable Hypervalent Iodine Reagentsmentioning

confidence: 99%

“…To overcome this limitation, various recyclable HVI(V) reagents have been reported in the literature. [90][91][92][93][94][95][96][97][98][99] The structures of these reagents are shown in Figure 10. In 2002, Thottumkara reported modified 2-iodoxybenzoic acid (mIBX) (202) as an efficient reagent for the oxidation of allylic and benzylic alcohols in water, affording the corresponding aldehydes in 60-96% yield.…”

Section: Recyclable Non-polymeric Hypervalent Iodine(v) Reagentsmentioning

confidence: 99%

“…Unreacted PIBS (204) and its reduced form PIBS-H can be recovered from the reaction mixture. 94,95 In an example reported by Sharma and co-workers, the HVI(V) reagent IBX and choline chloride/urea solvent were recycled in a three-component Ugi reaction. The reduced form of IBX can be recovered from the reaction mixture by filtration and converted back into IBX by treatment with aqueous Oxone ® .…”

Section: Recyclable Non-polymeric Hypervalent Iodine(v) Reagentsmentioning

confidence: 99%

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Recyclable Hypervalent Iodine Reagents in Modern Organic Synthesis

et al. 2022

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Hypervalent iodine (HVI) reagents have gained much attention as versatile oxidants because of their low toxicity, mild reactivity, easy handling, and availability. Despite their unique reactivity and other advantageous properties, stoichiometric HVI reagents are associated with the disadvantage of generating non-recyclable iodoarenes as waste/co-products. To overcome these drawbacks, the syntheses and utilization of various recyclable hypervalent iodine reagents have been established in recent years. This review summarizes the development of various recyclable non-polymeric, polymer-supported, ionic-liquid-supported, and metal–organic framework (MOF)-hybridized HVI reagents.1 Introduction2 Polymer-Supported Hypervalent Iodine Reagents2.1 Polymer-Supported Hypervalent Iodine(III) Reagents2.2 Polymer-Supported Hypervalent Iodine(V) Reagents3 Non-Polymeric Recyclable Hypervalent Iodine Reagents3.1 Non-Polymeric Recyclable Hypervalent Iodine(III) Reagents3.2 Recyclable Non-Polymeric Hypervalent Iodine(V) Reagents3.3 Fluorous Hypervalent Iodine Reagents4 Ionic-Liquid/Ion-Supported Hypervalent Iodine Reagents5 Metal–Organic Framework (MOF)-Hybridized Hypervalent Iodine Reagents6 Conclusion

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Section: Recyclable Non-polymeric Hypervalent Iodine(v) Reagentsmentioning

confidence: 99%

“…Unreacted PIBS ( 204 ) and its reduced form PIBS-H can be recovered from the reaction mixture. 94 95…”

Section: Non-polymeric Recyclable Hypervalent Iodine Reagentsmentioning

confidence: 99%

Section: Non-polymeric Recyclable Hypervalent Iodine Reagentsmentioning

confidence: 99%

Section: Recyclable Non-polymeric Hypervalent Iodine(v) Reagentsmentioning

confidence: 99%

Section: Recyclable Non-polymeric Hypervalent Iodine(v) Reagentsmentioning

confidence: 99%

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Recyclable Hypervalent Iodine Reagents in Modern Organic Synthesis

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Synthesis of Hypervalent Iodine Compounds for Oxidation Reactions

Zhdankin¹

2018

Patai's Chemistry of Functional Groups

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This chapter describes the preparation and properties of trivalent and pentavalent organoiodine compounds that are used as reagents for oxidation reactions. These compounds are represented by λ 3 ‐ and λ 5 ‐iodanes bearing one carbon ligand along with halogen, oxygen, or nitrogen ligands in a noncyclic or a cyclic (benziodoxole) structure. A detailed description of the best synthetic methods for the preparation of organoiodine(III) halides, iodosylarenes, [bis(acyloxy)iodo]arenes, aryliodine(III) sulfonates, amidoiodanes, imidoiodanes, and substituted benziodoxoles is provided. The preparation and structure of noncyclic and cyclic iodylarenes, including 2‐iodoxybenzoic acid (IBX) and Dess–Martin periodinane (DMP), are also discussed.

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Aqueous Mediated Reactions Involving Hypervalent Iodine Reagents

et al. 2022

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Several reactions mended by hypervalent iodine reagents have been developed in aqueous media recently. The evolution of reactions using hypervalent iodine reagents in aqueous medium is one of the most vital fields in organic synthesis to achieve one of the requirements of green chemistry. Hypervalent iodine reagents have the potential to replace toxic metals in numerous chemical reactions viz. oxidation reactions, coupling reactions, α-functionaliztion reactions, cyclization reactions and halogenations reactions etc. due to their stability, high selectivity, easy and simple experimentation, less toxic nature. In a chemical reaction solvents are required for several functions viz. in extractions, reactants solubility, washing and separation of final products. Water as a medium represents a safe, non-toxic, inexpensive and environmentally friendly alternative to toxic organic solvents for various organic reactions. The evolution of hypervalent iodine reagents with modified reactivities in aqueous phase now enable such chemical reactions which were thought to be illogical only a century ago. Therefore, in the present review, we summarize the various aqueous mediated reactions involving hypervalent iodine reagents.

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Potassium 4-Iodylbenzenesulfonate (PIBS): An Efficient Recyclable Hypervalent Iodine Reagent for Iodo-functionalization of Alkenes, Alkynes and Ketones

Cited by 3 publications

References 49 publications

Recyclable Hypervalent Iodine Reagents in Modern Organic Synthesis

Recyclable Hypervalent Iodine Reagents in Modern Organic Synthesis

Synthesis of Hypervalent Iodine Compounds for Oxidation Reactions

Aqueous Mediated Reactions Involving Hypervalent Iodine Reagents

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