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

Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 13, 2024

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

Language: Английский

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Enantioselective cross-dehydrogenative coupling enabled by organocatalysis

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(4), P. 1846 - 1875

Published: Jan. 1, 2024

Organocatalytic enantioselective cross-dehydrogenative coupling reaction provides a great opportunity for the synthesis of highly enantioenriched molecules. In this review, recent progress in field is summarized.

Language: Английский

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Halogen Bonds Formed by Halogen’s p/π-Hole in Molecules Help Shape Crystalline Materials

Crystal Growth & Design, Journal Year: 2025, Volume and Issue: unknown

Published: April 24, 2025

Language: Английский

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Advances in Catalytic Enantioselective Transformations Using Diaryliodonium Reagents

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 3096 - 3115

Published: Feb. 5, 2025

Language: Английский

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Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations

Chemical Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: March 7, 2025

Constructing chemical bonds under green sustainable conditions has drawn attention from environmental and economic perspectives. The dissociation of (hetero)aryl-halide is a crucial step most arylations affording (hetero)arene derivatives. Herein, we summarize the (hetero)aryl halides activation enabling direct (hetero)arylation trapping reagents construction highly functionalized (hetero)arenes benign conditions. strategies for aryl iodides are classified into (a) hypervalent iodoarene followed by functionalization thermal/photochemical conditions, (b) aryl-I bond in presence bases with/without organic catalysts promoters, (c) photoinduced presence/absence organophotocatalysts, (d) electrochemical direct/indirect electrolysis mediated organocatalysts mediators acting as electron shuttles, (e) electrophotochemical redox-active organocatalysts. These modes result exhibiting diverse reactivity formal cations/radicals/anions aryne precursors. coupling these reactive intermediates with leads to facile selective formation C-C C-heteroatom bonds. ecofriendly, inexpensive, functional group-tolerant offer alternatives transition metal-based catalysis.

Language: Английский

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Iodine(V)-Based Oxidants in Oxidation Reactions

Molecules, Journal Year: 2023, Volume and Issue: 28(13), P. 5250 - 5250

Published: July 6, 2023

The chemistry of hypervalent iodine reagents has now become quite valuable due to the reactivity these compounds under mild reaction conditions and their resemblance in chemical properties transition metals. environmentally friendly nature makes them suitable for Green Chemistry. Reagents with a dual nature, such as iodine(III) reagents, are capable electrophiles, while iodine(V) known strong oxidant behavior. Various including IBX DMP have been used oxidants organic synthesis either stoichiometric or catalytic amounts. In this review article, we describe various oxidation reactions induced by reported past decade.

Language: Английский

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Hypervalent Iodine Compounds in Carbohydrate Chemistry: Glycosylation, Functionalization and Oxidation

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(25)

Published: Feb. 13, 2024

Abstract This mini review article provides an overview on the use of hypervalent iodine compounds (HICs) in carbohydrate synthesis, focusing their chemistry and recent applications. HICs are similar to transition metals reactivity but have added benefit being environmentally benign, therefore commonly used as selective oxidants eco‐friendly reagents organic synthesis. Herein, we summarize various synthetic uses reactions such glycosylation, oxidations, functionalization, C−C bond‐forming reactions. The goal this is illustrate advantages versatility using sustainable alternative heavy chemistry.

Language: Английский

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Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2891 - 2920

Published: Nov. 13, 2024

Diaryliodonium salts have become widely recognized as arylating agents in the last two decades. Both, symmetrical and unsymmetrical forms of these serve effective electrophilic reagents various organic syntheses. The use diaryliodoniums C–C carbon–heteroatom bond formations, particularly under metal-free conditions, has further enhanced popularity reagents. In this review, we concentrate on arylation reactions involving carbon other heteroatoms, encompassing rearrangement absence any metal catalyst, summarize advancements made five years.

Language: Английский

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Copper-Catalyzed/Hypervalent Iodine-Mediated Functionalization of Unactivated Compounds

Catalysts, Journal Year: 2023, Volume and Issue: 13(9), P. 1243 - 1243

Published: Aug. 26, 2023

The functionalization of unactivated substrates through the combination copper catalysts and hypervalent iodine reagents represents a versatile tool in organic synthesis to access various classes compounds. derivatives can be used simply as oxidizing agents regenerate catalytic species or they associate starting material. In this review, special attention will paid methodologies which provide introduction nucleophiles into reagent by use suitable benziodoxol(on)es iodonium salts. Many reactions concern C- N-arylations, but may also involve formation different carbon–carbon carbon–nitrogen bonds, carbon–oxygen well carbon–halogen carbon–phosphorus bonds.

Language: Английский

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A Focused Review on Oxidation of Hydrazones Using Hypervalent Iodine Reagents

ChemistrySelect, Journal Year: 2024, Volume and Issue: 10(1)

Published: Dec. 31, 2024

Abstract Hydrazones are described as synthetic equivalents to the carbonyl group and possess high synthon value. Herein, we compile oxidative transformation of hydrazones using ecologically economically benign hypervalent iodine reagents last decade. In this field, development C─H functionalization reactions leading formation heterocycles or functionalized is a major advancement in recent years. The properties exploited form many bioactive (pyrazole, pyrazoline, pyridazine, 1,2,4‐triazole, 1,2,3‐tiazole, 1,3,4‐oxadiazole, tetrazine, tetrazole, pyrrole) through intramolecular intermolecular C─N, C─O, N─N coupling. Functionalized also afforded via tandem cascade transfer/cyclization reactions. transfer perfluoroalkyl, sulfoximidoyl, aryl, halogen groups achieved donors oxidants combination with other group‐donating agents. Togni reagent preferred choice for trifluoromethyl donation, without metal catalyst. Moreover, rearrangement such acyl migration diazotization achieved.

Language: Английский

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