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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Applications of innovative synthetic strategies in anticancer drug Discovery: The Driving Force of new chemical reactions

Bioorganic & Medicinal Chemistry Letters, Journal Year: 2025, Volume and Issue: 119, P. 130096 - 130096

Published: Jan. 9, 2025

Language: Английский

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Rh(iii)-catalyzed C–H annulation of sulfoxonium ylides with iodonium ylides towards isocoumarins

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(5), P. 1112 - 1116

Published: Jan. 1, 2022

The direct synthesis of isocoumarin skeletons has been realized through the Rh( iii )-catalyzed [3 + 3] annulation sulfoxonium ylides and iodonium under mild conditions.

Language: Английский

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Accessing 7,8-Dihydroquinoline-2,5-diones via Rh-Catalyzed Olefinic C–H Activation/[4+2] Cyclization

Organic Letters, Journal Year: 2024, Volume and Issue: 26(24), P. 5136 - 5140

Published: June 7, 2024

Herein, we report a rhodium-catalyzed C–H activation/[4+2] cyclization reaction between α,β-unsaturated amides and iodonium ylides for the synthesis of novel 7,8-dihydroquinoline-2,5-diones analogues. This protocol provides series pyridones fused with saturated cycles good functional group compatibility, water air tolerance, to excellent yields under mild green conditions. Additionally, scale-up can be smoothly performed as low 0.25 mol % catalyst loading. Recycling experiments different transformation were also carried out demonstrate potential synthetic utility this protocol.

Language: Английский

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Synthesis of CF₃–Isoquinolinones and Imidazole-Fused CF₃–Isoquinolinones Based on C–H Activation-Initiated Cascade Reactions of 2-Aryloxazolines

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10180 - 10196

Published: July 4, 2024

Presented herein are novel syntheses of CF

Language: Английский

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Iodonium ylides: an emerging and alternative carbene precursor for C–H functionalizations

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 21(1), P. 24 - 38

Published: Nov. 23, 2022

The metal-catalyzed successive activation and functionalization of arene/heteroarene is one the most fundamental transformations in organic synthesis leads to privileged scaffolds natural products, pharmaceuticals, agrochemicals, fine chemicals. Particularly, transition-metal-catalyzed C-H arenes with carbene precursors via metal migratory insertion has been well studied. As a result, diverse have evaluated, such as diazo compounds, sulfoxonium ylides, triazoles, etc. In addition, there significant developments use iodonium ylides recent years, these reactions proceed high efficiencies selectivities. This review provides comprehensive overview functionalizations, including scope, limitations, their potential synthetic applications.

Language: Английский

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Rh(iii)-catalyzed C–H/C–C bond annulation of enaminones with iodonium ylides to form isocoumarins

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(97), P. 13483 - 13486

Published: Jan. 1, 2022

A straightforward approach to synthesise isocoumarins via Rh(III)-catalyzed C-H/C-C bond activation/annulation cascade of enaminones and iodonium ylides has been explored. The established protocol is characterized by an exceedingly simple reaction system, high regioselectivity good functional group tolerance. Moreover, this strategy may provide a new route cleavage the C(sp2)-C(O) unstrained ketones.

Language: Английский

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Rh(iii)-catalyzed cascade annulation reaction of N,N-dimethyl enaminones with iodonium ylides to give substituted isocoumarins

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(26), P. 12274 - 12278

Published: Jan. 1, 2023

A wide variety of isocoumarin derivatives are easily constructed via a Rh( iii )-catalyzed C–H bond activation/annulation cascade reaction.

Language: Английский

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Synthesis of Tetrahydrocarbazol-4-ones via Rh(III)-Catalyzed C–H Activation/Annulation of Arylhydrazines with Iodonium Ylides

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(12), P. 8142 - 8150

Published: June 8, 2022

The rhodium(III)-catalyzed C–H activation followed by intramolecular annulation reactions between arylhydrazines and iodonium ylides under suitable conditions has been described. Tetrahydrocarbazol-4-ones are readily achieved with moderate to excellent yields. synthetic protocol features a wide range of substrates high functional group tolerance. gram-scale reaction derivatization the product demonstrate practicality utilization this method.

Language: Английский

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Recent Advances in Site Selective Transformations of β-Enaminones via C-H Functionalization/Annulation

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

β-Enaminone transformation strategies are widely employed in the synthesis of numerous biologically active drugs and natural products, highlighting their significance medicinal chemistry.

Language: Английский

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