New, Milder Hypervalent Iodine Oxidizing Agent: Using μ-Oxodi(phenyliodanyl) Diacetate, a (Diacetoxyiodo)benzene Derivative, in the Synthesis of Quinones

Peng, Hao; Bryan, J. G. H.; Henson, William; Zhdankin, Viktor V.; Gandhi, Kushal; David, Samuel

doi:10.1021/acs.jchemed.8b00636

Cited by 4 publications

(2 citation statements)

References 36 publications

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“…[107] Peng et al in 2019 developed a method for the oxidation of 2,3,5-trimethyl-1,4-hydroquinone and 1,2,4-trimethoxy benzene to afford corresponding substituted 1,4-benzoquinones (Scheme 82) in water using μ-oxodi(phenyliodanyl) diacetate, a (diacetooxyiodo) benzene-based oxidizing reagent in order to introduce their organic laboratory students to extremely popular and environmentally benign hypervalent iodine chemistry. [115] Mechanism of this reaction involves reaction of the nucleophile (hydroquinone) with above mentioned hypervalent iodine reagent resulting in the formation of oxidized nucleophile (quinone) and reduced iodine in the form of PhI.…”

Section: Nuclear Oxidation Reactionsmentioning

confidence: 99%

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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Section: Nuclear Oxidation Reactionsmentioning

confidence: 99%

Aqueous Mediated Reactions Involving Hypervalent Iodine Reagents

et al. 2022

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“…Hypervalent iodine can be used as an initiator to trigger various chemical reactions, functioning like a transition metal catalyst, and this reagent has been widely applied to drug synthesis and total synthesis of natural products 44 – 48 . Considering the potential value of R–ONH 2 compounds, we herein report an approach to constructing C–O bonds in unactivated alkanes, cyanides, ethers, and thioethers via a CDC reaction with NHPI in the presence of iodobenzene diacetate as a radical initiator (Fig.…”

Section: Introductionmentioning

confidence: 99%

Iodine(III) promotes cross-dehydrogenative coupling of N-hydroxyphthalimide and unactivated C(sp3)–H bonds

Han

et al. 2021

Commun Chem

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Cross-dehydrogenative coupling reactions provide a method to construct new chemical bonds by direct C–H activation without any pre-functionalization. Compared to functionalization of a C–H bond α- to ether oxygen, α- to carbonyl, or at a benzylic position, functionalization of unactivated hydrocarbons is difficult and often requires high temperatures, a transition-metal catalyst, or a superstoichiometric quantity of volatile, toxic, and explosive tert-butylhydroperoxide. Here, a cross-dehydrogenative C–O coupling reaction of N-hydroxyphthalimide with unactivated alkanes, nitriles, ethers, and thioethers has been realized by using iodobenzene diacetate as the radical initiator. The current protocol enables efficient functionalization of unactivated hydrocarbons and nitriles through inert C(sp3)–H bond activation under mild reaction conditions. O-substituted NHPI derivatives are generated in good yields under metal-free conditions.

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Synthesis of Dihydropyrrole Derivatives by Oxidative Functionalization of 2-Amino-4H-Chromenes Using Hypervalent Iodine Reagents

Indukuri

Potuganti

Nanubolu

et al. 2021

Synlett

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An efficient simple, metal-free, one-pot protocol for the synthesis of dihydropyrrole derivatives has been achieved via sequential addition of iodobenzenediacetate and secondary amine to 2-amino-4H- pyran derivatives. The one-pot protocol proceeds through tandem oxidative functionalization, rearrangement, and ring contraction to provide an entirely new strategy for the construction of the dihydropyrrole skeleton.

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New, Milder Hypervalent Iodine Oxidizing Agent: Using μ-Oxodi(phenyliodanyl) Diacetate, a (Diacetoxyiodo)benzene Derivative, in the Synthesis of Quinones

Cited by 4 publications

References 36 publications

Aqueous Mediated Reactions Involving Hypervalent Iodine Reagents

Aqueous Mediated Reactions Involving Hypervalent Iodine Reagents

Iodine(III) promotes cross-dehydrogenative coupling of N-hydroxyphthalimide and unactivated C(sp3)–H bonds

Synthesis of Dihydropyrrole Derivatives by Oxidative Functionalization of 2-Amino-4H-Chromenes Using Hypervalent Iodine Reagents

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