A decade of lessons in the activation of ArIL<sub>2</sub> species

Tania,; Sceney, Marcus; Dutton, Jason L.

doi:10.1039/d3sc06588j

Chem. Sci.

2024

DOI: 10.1039/d3sc06588j

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A decade of lessons in the activation of ArIL₂ species

Tania,

Marcus Sceney,

Jason L. Dutton

Abstract: Hypervalent iodine(III) compounds of the general structure ArIL2 are widely used as oxidizing agents for a variety of applications across both organic and inorganic chemistry. Considerable work has been done...

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Cited by 2 publications

References 99 publications

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PIDA as an Iodinating Reagent: Visible‐Light‐Induced Iodination of Pyrazolo[1,5‐a]pyrimidines and Other Heteroarenes

Paul,

Das,

Choudhuri

et al. 2024

Chemistry An Asian Journal

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We have developed a visible‐light‐mediated convenient and efficient strategy for the iodination of heteroarenes using diacetoxyiodobenzene (PIDA) under photocatalyst‐free conditions. This unique approach is the first report on photocatalytic C‐H iodination employing PIDA as the iodinating agent. The new photocatalyst‐free strategy is applicable to a wide range of pyrazolo[1,5‐a]pyrimidine derivatives with various functionalities. Iodination of other electron‐rich heterocycles like imidazo[1,2‐a]pyridine, imidazo[1,2‐a]pyrimidine, imidazo[2,1‐b]thiazole, benzo[d]imidazo[2,1‐b]thiazole, and pyrazoles has been accomplished employing this benign protocol. The usefulness of 3‐iodo pyrazolo[1,5‐a]pyrimidine as a synthetic intermediate in synthesizing various functionalized pyrazolo[1,5‐a]pyrimidines has been demonstrated.

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PIDA as an Iodinating Reagent: Visible‐Light‐Induced Iodination of Pyrazolo[1,5‐a]pyrimidines and Other Heteroarenes

Paul,

Das,

Choudhuri

et al. 2024

Chemistry An Asian Journal

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Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

Yoshimura,

Zhdankin

2024

Chem. Rev.

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Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. Hypervalent iodine reagents are commonly used in synthetically important halogenations, oxidations, aminations, heterocyclizations, and various oxidative functionalizations of organic substrates. Iodonium salts are important arylating reagents, while iodonium ylides and imides are excellent carbene and nitrene precursors. Various derivatives of benziodoxoles, such as azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, and alkenylbenziodoxoles have found wide application as group transfer reagents in the presence of transition metal catalysts, under metal-free conditions, or using photocatalysts under photoirradiation conditions. Development of hypervalent iodine catalytic systems and discovery of highly enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important recent achievement in the field of hypervalent iodine chemistry. Chemical transformations promoted by hypervalent iodine in many cases are unique and cannot be performed by using any other common, non-iodine-based reagent. This review covers literature published mainly in the last 7−8 years, between 2016 and 2024.

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A decade of lessons in the activation of ArIL₂ species

Abstract: Hypervalent iodine(III) compounds of the general structure ArIL2 are widely used as oxidizing agents for a variety of applications across both organic and inorganic chemistry. Considerable work has been done...

Cited by 2 publications

References 99 publications

PIDA as an Iodinating Reagent: Visible‐Light‐Induced Iodination of Pyrazolo[1,5‐a]pyrimidines and Other Heteroarenes

PIDA as an Iodinating Reagent: Visible‐Light‐Induced Iodination of Pyrazolo[1,5‐a]pyrimidines and Other Heteroarenes

Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

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A decade of lessons in the activation of ArIL2 species

Abstract: Hypervalent iodine(III) compounds of the general structure ArIL2 are widely used as oxidizing agents for a variety of applications across both organic and inorganic chemistry. Considerable work has been done...

Cited by 2 publications

References 99 publications

PIDA as an Iodinating Reagent: Visible‐Light‐Induced Iodination of Pyrazolo[1,5‐a]pyrimidines and Other Heteroarenes

PIDA as an Iodinating Reagent: Visible‐Light‐Induced Iodination of Pyrazolo[1,5‐a]pyrimidines and Other Heteroarenes

Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

Contact Info

Product

Resources

About

A decade of lessons in the activation of ArIL₂ species