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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Oxidation of N-trifluoromethylthio sulfoximines using NaOCl·5H₂O

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(10), P. 2012 - 2020

Published: Jan. 1, 2024

N -Trifluoromethylthio sulfoximines were oxidized using NaOCl·5H 2 O to the corresponding novel -trifluoromethylsulfaneylidene in high yields and with excellent green metrics.

Language: Английский

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Visible-Light-Mediated α-Ketoacylations of NH-Sulfoximines with gem-Difluoroalkenes

Organic Letters, Journal Year: 2022, Volume and Issue: 24(3), P. 907 - 911

Published: Jan. 18, 2022

A photochemical approach for the preparation of α-keto-N-acyl sulfoximines from NH and gem-difluoroalkenes has been developed. In presence NBS, reactions proceed in air without need a photocatalyst or additional oxidant. Results mechanistic studies suggest that two oxygens products stem water dioxygen.

Language: Английский

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Advances in the photoredox catalysis of S(VI) compounds

Tetrahedron, Journal Year: 2022, Volume and Issue: 111, P. 132711 - 132711

Published: March 2, 2022

Language: Английский

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Photocatalytic Synthesis of Difluoroacetoxy-containing Sulfoximines

Organic Letters, Journal Year: 2021, Volume and Issue: 23(17), P. 6891 - 6894

Published: Aug. 20, 2021

[Bis(difluoroacetoxy)iodo]benzene and NH-sulfoximines react to give new hypervalent iodine(III) reagents, which under photocatalysis transfer difluoroacetoxy sulfoximidoyl groups styrenes with high regioselectivity. The results of mechanistic investigations suggest the intermediacy radicals reveal importance group on iodine reagent.

Language: Английский

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Electrochemical N‐Aroylation of Sulfoximines by Using Benzoyl Hydrazines with H₂ Generation

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 30(9)

Published: Nov. 22, 2023

Abstract Developed here is a robust electrochemical cross‐coupling reaction between aroyl hydrazine and NH ‐sulfoximine via concomitant cleavage formation of C(sp 2 )−N bonds with the evolution H N as innocuous by‐products. This sustainable protocol avoids use toxic reagents occurs at room temperature. The proceeds generation an sulfoximidoyl radical anodic oxidation under constant current electrolysis (CCE), affording ‐aroylated sulfoximine. strategy applied to late‐stage sulfoximidation L‐menthol, (−)‐borneol, D‐glucose, vitamin‐E derivatives, marketed drugs such probenecid, ibuprofen, flurbiprofen, ciprofibrate, sulindac. In addition, present methodology mild, high functional group tolerance broad substrate scope scalable.

Language: Английский

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Planarizable Push‐Pull Probes with Sulfoximine‐Bridged Dithienothiophene Acceptors

Helvetica Chimica Acta, Journal Year: 2021, Volume and Issue: 105(2)

Published: Dec. 22, 2021

Abstract Contrary to sulfides, sulfoxides or sulfones, sulfoximines have been mostly neglected in the design of fluorescent probes until recently. In this study, we elaborate systematically on sulfoximine acceptors flipper probes. Fluorescent flippers introduced as mechanosensitive image membrane order and tension. They consist twisted dithienothiophene dimers with sulfide sulfone bridges produce essential primary dipole coupled push‐pull system. The objective study was replace acceptor by a series sulfoximines. This is intriguing synthetic challenge worthwhile because extra nitrogen substituent offers variability that attractive understand control performance new provide corroborative evidence for importance planarizable probe. Partitioning into differently ordered membranes positioning within these different shown correlate directly dramatically fluorescence lifetimes mechanosensitivity. Sufficient partitioning confirmed particularly important tension probe compression ground state. Compared conventional homolog, best has more red‐shifted absorption emission maxima, longer lifetime cell membranes, larger difference upon application

Language: Английский

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Copper-Catalyzed Sulfonylation Reaction of NH-Sulfoximines with Aryldiazonium Tetrafluoroborates and Sulfur Dioxide: Formation of N-Sulfonyl Sulfoximines

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(4), P. 2322 - 2333

Published: Jan. 26, 2023

An efficient and practical SO2 insertion protocol of NH-sulfoximines with aryldiazonium tetrafluoroborates DABSO toward N-sulfonyl sulfoximines has been developed under mildly basic conditions. This transformation features easy operation, readily available substrates, mild A tentative mechanism is proposed, which indicates that the would be radical donors standard reaction The aryl produced in situ from diazonium salts trapped by to generate an arylsulfonyl then undergo further final sulfoximines.

Language: Английский

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Green One-Pot Syntheses of 2-Sulfoximidoyl-3,6-dibromo Indoles Using N-Br Sulfoximines as Both Brominating and Sulfoximinating Reagents

Molecules, Journal Year: 2023, Volume and Issue: 28(8), P. 3380 - 3380

Published: April 11, 2023

A green one-pot 2,3,6-trifunctionalization of N-alkyl/aryl indoles was achieved by adding three equivalents N-Br sulfoximine to the indole solution. variety 2-sulfoximidoyl-3,6-dibromo were prepared with 38-94% yields using sulfoximines as both brominating and sulfoximinating reagents. Based on results controlled experiments, we propose that a radical substitution involving 3,6-dibromination 2-sulfoximination occurs in reaction process. This is first time one pot has been achieved.

Language: Английский

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Metal-free synthesis of N-vinyl sulfoximines via DABCO-participated Michael addition of terminal carbonyl alkynes with N-chlorosulfoximines

Tetrahedron, Journal Year: 2022, Volume and Issue: 129, P. 133142 - 133142

Published: Nov. 12, 2022

Language: Английский

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