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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Metal-Free Electrocatalytic Synthesis of Fused Azabicycles from N-Allyl Enamine Carboxylates

Organic Letters, Journal Year: 2024, Volume and Issue: 26(13), P. 2651 - 2655

Published: March 22, 2024

An electrocatalytic approach to access structurally significant azabicyclic scaffolds from N-allyl enamine carboxylates is illustrated. This metal-free method functions exclusively with a catalytic amount of iodide, strategically employed electrochemically generate reactive hypervalent iodine species, which facilitates the cascade bicyclization processes enhanced precision and efficiency. Excellent functional group compatibility was observed, enabling synthesis series azabicycle derivatives. Detailed mechanistic electrochemical studies enhance comprehension reaction sequence.

Language: Английский

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Imino-λ³-iodane-Triggered Oxidative Ring-Opening of 2H-Indazoles to ortho-N-Acylsulfonamidated Azobenzenes

Organic Letters, Journal Year: 2023, Volume and Issue: 25(22), P. 4183 - 4187

Published: May 31, 2023

An iminoiodane-enabled oxidative ring-opening of 2H-indazoles via C-N bond cleavage has been developed under metal-free reaction conditions. This methodology afforded a new array unsymmetrical ortho-N-acylsulfonamidated azobenzenes with wide functional group tolerance in good yields. The potentially proceeds through the formation zwitterionic adduct, which is formed by between and iminoiodane.

Language: Английский

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Cu-Catalyzed Regioselective C–H Amination of 2H-Indazoles for the Synthesis of Indazole-Containing Indazol-3(2H)-ones

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 5731 - 5744

Published: March 30, 2023

A copper-catalyzed C3 amination of 2H-indazoles with and indazol-3(2H)-ones under mild conditions was developed. series indazole-containing indazol-3(2H)-one derivatives were produced in moderate to excellent yields. The mechanistic studies suggest that the reactions probably proceed through a radical pathway.

Language: Английский

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Electrochemical C3 acyloxylation reactions of 2H-indazoles with carboxylic acids via C(sp²)–O coupling

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(20), P. 8117 - 8123

Published: Jan. 1, 2023

The electrochemical C3 acyloxylation reactions of 2 H -indazoles with carboxylic acids in the presence K CO 3 were successfully developed, which green and sustainable without transition-metal catalysts stoichiometric oxidants.

Language: Английский

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An Electrochemical Oxo‐amination of 2H‐Indazoles: Synthesis of Symmetrical and Unsymmetrical Indazolylindazolones

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 30(12)

Published: Dec. 26, 2023

We have established a supporting-electrolyte free electrochemical method for the synthesis of indazolylindazolones through oxygen reduction reaction (eORR) induced 1,3-oxo-amination 2H-indazoles where 2H-indazole is used as both aminating agent well precursor indazolone. Moreover, we merged indazolone and indazole to get unsymmetrical direct cross-dehydrogenative coupling (CDC). This exogenous metal-, oxidant- catalyst-free protocol delivered number multi-functionalized products with high tolerance diverse functional groups.

Language: Английский

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One-pot synthesis of 4-(imidazol-1-yl)indole derivatives through a sequential dearomatization and Ag-catalyzed cyclization/Cs₂CO₃-mediated addition/aromatization reaction

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(20), P. 4245 - 4256

Published: Jan. 1, 2023

A convenient one-pot assembly of 4-(imidazol-1-yl)indole derivatives from easily accessible o-alkynylanilines and imidazoles has been developed. The sequential dearomatization Ag(I)-catalyzed cyclization/Cs2CO3-mediated conjugate addition/aromatization cascade reactions exhibit high efficiency excellent selectivity. combined use a silver(I) salt cesium carbonate is significant for facilitating this domino transformation. products could be converted to the corresponding might valuable in biological chemistry medicinal science.

Language: Английский

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Skeletal Editing through Molecular Recombination of 2H‐Indazoles to Azo‐Linked‐Quinazolinones

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 30(10)

Published: Nov. 29, 2023

Abstract A new protocol by the combinatory use of two equivalent indazoles starting material with one being carbon source via its C3‐reactivity and other, coupling partner has been developed for selectfluor‐mediated single atom skeletal editing 2 H ‐indazoles. The azo‐linked‐2,3‐disubstituted quinazolin‐4‐one derivatives were obtained through a insertion between nitrogens indazole ring simultaneous oxidation at C3 position both moieties. Mechanistic investigations reveal that amidic carbonyl oxygen product is derived from water reaction proceeds in‐situ generated N ‐centred indazolone radical intermediate.

Language: Английский

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Hypervalent Iodine Mediated Synthesis of 2‐Aminobenzazoles and 2‐Aminobenzothiazoles

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(6)

Published: April 6, 2024

Abstract The hypervalent iodine mediated, silica gel promoted synthesis of 2‐aminobenzazoles and 2‐aminobenzothiazole derivatives under metal‐free mild conditions within short time (30 min) has been developed. Under this process, PhI(COOCF 3 ) 2 (PIFA) or PhI(COOCH (PIDA) acts as an oxidant radical initiator direct activated the ortho ‐C−H bond substrate, weakly lewis acid effectively increased reactivity reaction system. This method is compatible with various arylurea arylthiourea substrates, which green, efficient, simple to operate suitable for practical application.

Language: Английский

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PIFA-mediated intramolecular N-arylation of 2-aminoquinoxalines to afford indolo[2,3-b]quinoxaline derivatives

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(28), P. 5803 - 5808

Published: Jan. 1, 2024

We present the PIFA-mediated intramolecular

Language: Английский

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