Introduction to hypervalent iodine chemistry. Part 3

Zhdankin, Viktor V.

doi:10.24820/ark.5550190.p001.488

Arkivoc

2022

DOI: 10.24820/ark.5550190.p001.488

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Introduction to hypervalent iodine chemistry. Part 3

Viktor V. Zhdankin¹

Abstract: This special issue of Arkivoc is for "Hypervalent Iodine Chemistry"This short overview provides a brief introduction to Part 3 of the Arkivoc series of issues on Hypervalent Iodine (HI) Chemistry. A summary of topics covered in the 2020 and 2021 HI issues of Arkivoc is provided and recent literature reviews on Hypervalent Iodine Chemistry are referenced. Hypervalent iodine reagents and catalysts are intensively used in modern organic chemistry as mild, environmentally safe, and economical alternative to heavy … Show more

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Cited by 4 publications

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Hypervalent Iodine‐Mediated Azidation Reactions

et al. 2022

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Organic azides have found wide application in various fields of science and technology. This review summarizes recently developed approaches to the direct, one‐step synthesis of diverse organic azides utilizing hypervalent iodine reagents. The first part of review deals with the azidation using unstable azidoiodinanes generated in situ from common hypervalent iodine reagents (such as diacetoxyiodobenzene or iodosylbenzene) and a source of azide anion (TMSN3 or NaN3). The second part of review is dedicated to the application of stable azidobenziodoxoles as useful azidating reagents that allow selective direct azidation of C−H bonds or double carbon‐carbon bonds under mild reaction conditions. The use of azidobenziodoxoles eliminates the main disadvantages of the traditional approaches to organic azides, such as the need in pre‐functionalization of organic substrates and harsh reaction conditions. Synthetic application of azidobenziodoxoles made possible direct selective azidation of a plethora of organic substrates including complex molecules at the late synthetic stage.

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Hypervalent Iodine‐Mediated Azidation Reactions

et al. 2022

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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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Organocatalytic synthesis of β-enaminyl radicals as single-electron donors for phenyliodine(iii) dicarboxylates: direct one-pot alkylation–aminoxidation of styrenes

et al. 2023

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Introduction to hypervalent iodine chemistry. Part 3

Cited by 4 publications

References 38 publications

Hypervalent Iodine‐Mediated Azidation Reactions

Hypervalent Iodine‐Mediated Azidation Reactions

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

Organocatalytic synthesis of β-enaminyl radicals as single-electron donors for phenyliodine(iii) dicarboxylates: direct one-pot alkylation–aminoxidation of styrenes

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