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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Electrochemical oxidative CF₃ radical-induced lactonization and etherification of terminal and internal alkenes

RSC Advances, Journal Year: 2025, Volume and Issue: 15(19), P. 15302 - 15309

Published: Jan. 1, 2025

Introducing CF 3 groups boosts drug properties by enhancing metabolic stability and bioavailability. This study reports an electrochemical oxidative difunctionalization of flexible alkenes to form -substituted lactones cyclic ethers.

Language: Английский

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Visible‐Light‐Catalyzed Formal [3+2] Annulation‐Aromatization of Amidines with Isoquinolinium N‐Ylides: Access to Imidazo[2,1‐a]isoquinolines

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(21), P. 3629 - 3636

Published: Sept. 21, 2023

Abstract A visible‐light‐catalyzed formal [3+2] annulation‐aromatization reaction for the synthesis of various substituted imidazo[2,1‐ a ]isoquinolines from amidines with stabilized isoquinolinium N ‐ylides in presence bases is developed. The procedure reported here involves direct C−H activation and formation C−C/C−N bonds one‐pot. mechanism probed by radical‐trapping experiment, fluorescence quenching, light on/off experiments. late‐stage modification experiments provide potential applications field organic medicinal chemistry chemists.

Language: Английский

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Palladium–Copper-Catalyzed Oxidative Intermolecular [2 + 2 + 2] Coupling–Annulation: Regioselective Synthesis of Multiaryl-Substituted Benzenes

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 4579 - 4594

Published: March 20, 2024

A palladium-catalyzed intermolecular [2 + 2 2] oxidative coupling–annulation of terminal alkenes and alkynes using copper(II) as the oxidant has been developed through direct C–C bond formation. These reactions provide effective access to multiaryl-substituted benzenes with high regioselectivity in absence any ligands. The features this protocol are broad substrate scope, atom step economy. aggregation-induced emission properties selected products were further investigated. synthesized may be worth exploring for applications fields advanced functional materials or drugs.

Language: Английский

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Synthesis of Primary and Secondary Amines via Electrochemical Reduction of Hydrazines

Organic Letters, Journal Year: 2024, Volume and Issue: 26(51), P. 11123 - 11128

Published: Dec. 13, 2024

We herein introduce an electrochemical route for the N–N bond cleavage of hydrazines. This mild and green methodology utilized readily available mono- 1,1-disubstituted hydrazines or their HCl salts as starting materials to access a broad scope primary secondary amines in high yields. The mechanistic investigation suggests that amine product is formed by consecutive SET reduction, utilization hydrazine salt important providing sufficient conductivity acidity facilitate this reaction.

Language: Английский

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An aerobic copper-catalyzed multi-component reaction strategy for N′,N′-diaryl acylhydrazine synthesis: reactions and mechanism

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(4), P. 1132 - 1139

Published: Dec. 20, 2023

A sequential multi-component reaction of aldehydes and aryl hydrazines for the synthesis N' , -diaryl acylhydrazines with high regioselectivity has been achieved via an aerobic copper-catalyzed process.

Language: Английский

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Visible Light Mediated Chemoselective Hydroxylation of Benzylic Methylenes

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2656 - 2664

Published: Feb. 7, 2024

We have developed a metal-free photocatalytic selective hydroxylation of benzylic methylenes to secondary alcohols. This approach utilizes low-cost eosin Y as photocatalyst, O2 green oxidant, and inexpensive triethylamine inhibitor for overoxidation. The mild reaction conditions enable the production alcohols with 56–95% yields, making it promising environmental-friendly method synthesis from methylenes.

Language: Английский

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Photocatalytic One-Pot Three-Component Reaction for the Regioselective Synthesis of Bromo-Substituted Pyrazoles

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16809 - 16827

Published: Nov. 1, 2024

A photocatalytic three-component cascade reaction of readily available enaminones, hydrazines, and CBr4 for the synthesis bromo-substituted pyrazoles in one pot has been demonstrated. This strategy involves intermolecular C-N/C-Br bond formation represents an efficient approach to construction 4-bromo-substituted with high regioselectivity, broad substrate scope, good functional group tolerance, convenient operation, mild conditions. Mechanistic investigations show that this proceeds via cyclization enaminones followed by a regioselective bromination using as "Br" source.

Language: Английский

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Recent applications of phenyl hydrazine in photoinduced chemical transformations

Synthetic Communications, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 23

Published: Dec. 3, 2024

Phenyl hydrazine has attracted attention in photoredox catalytic synthetic strategies for the formation of carbon-carbon (C-C) bond and Carbon-Heteroatom (C-N, C = N, C-P, C-S, S-N) bonds, because low cost ease availability make it a promising alternative method typical transition metal complex-based photocatalyzed synthesis. In this review, we have focused on recent radical coupling ­reactions phenyl via photochemical to form carbon–carbon carbon–heteroatom (N, P, S) bonds along with mechanism involved their reaction.

Language: Английский

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Overview of Phenylhydrazine‐Based Organic Transformations

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

Published: Dec. 30, 2024

Abstract Phenylhydrazines, comprised of a phenyl group attached with hydrazine unit, contribute potentially to organic synthetic transformations. Because the myriad applications, last decade has witnessed considerable upsurge interest perform various reactions catalyzed/mediated/promoted by phenylhydrazines. Some these have shown high regioselectivity in short reaction time under mild conditions. The emergence innumerable transformations utilizing phenylhydrazine unleashed numerous openings for development diverse heterocyclic scaffolds. Given importance this valuable chemical entity, review highlights methodologies Moreover, present article will considerably synthesis as well pharmaceutical chemistry. Academically, be interesting and informative researchers attempting develop new routes structures.

Language: Английский

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