Visible light-driven C–H arylation of heteroarenes with aryl diazonium salts in water catalyzed by a Z-scheme CuInS₂/K-C₃N₄ heterojunction

Green Chemistry, Год журнала: 2024, Номер 26(8), С. 4803 - 4810

Опубликована: Янв. 1, 2024

Z-scheme CuInS 2 /K-C 3 N 4 heterojunction has been designed and confirmed as efficient heterogeneous photocatalyst for arylation of heteroarenes with aryl diazonium salts in water under visible light irradiation to give arylated high yields.

Язык: Английский

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Modern photo- and electrochemical approaches to aryl radical generation

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(18), С. 5232 - 5277

Опубликована: Янв. 1, 2024

This review describes recent advances in the generation of aryl radicals using light and electricity. Such modern techniques allow for efficient energy resource utilization, thus providing more sustainable radical arylation methods.

Язык: Английский

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Direct C(sp3)-H functionalization with aryl and alkyl radicals as intermolecular hydrogen atom transfer (HAT) agents

Chemical Communications, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Recent years have witnessed the emergence of direct intermolecular C(sp

Язык: Английский

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Mechanochemical Synthesis of α‐halo Alkylboronic Esters

Advanced Science, Год журнала: 2024, Номер 11(33)

Опубликована: Июль 3, 2024

α-halo alkylboronic esters, acting as ambiphilic synthons, play a pivotal role versatile intermediates in fields like pharmaceutical science and organic chemistry. The sequential transformation of carbon-boron carbon-halogen bonds into broad range carbon-X allows for programmable bond formation, facilitating the incorporation multiple substituents at single position streamlining synthesis complex molecules. Nevertheless, synthetic potential these compounds is constrained by limited reaction patterns. Additionally, conventional methods often necessitate use bulk toxic solvents, exhibit sensitivity to air/moisture, rely on expensive metal catalysts, involve extended times. In this report, ball milling technique introduced that overcomes limitations, enabling external catalyst-free multicomponent coupling aryl diazonium salts, alkenes, simple halides. This approach offers general straightforward method obtaining diverse array thereby paving way extensive utilization synthons fine chemicals.

Язык: Английский

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Direct C–H sulfonylation of hydrazones involving the insertion of SO₂

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(15), С. 4284 - 4289

Опубликована: Янв. 1, 2024

A three-component reaction of aldehyde-derived hydrazones with DABSO and aryldiazonium tetrafluoroborates is described. Moreover, the photocatalyzed sulfonylation can also be achieved from sulfonyl chlorides.

Язык: Английский

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Light‐Induced Direct Decarboxylative Functionalization of Aromatic Carboxylic Acids

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(21), С. 4263 - 4273

Опубликована: Авг. 28, 2024

Abstract Aryl radicals are important intermediates in organic synthesis. The generation of these reactive species via direct decarboxylation inexpensive and readily available aromatic carboxylic acids is an attractive goal. However, such a process intrinsically exhibits high energy barriers to overcome, which consequence usually require precious metal catalysis, stoichiometric oxidants harsh conditions, suffering from limitations as poor functional group tolerance low atom economy. In recent years, photochemical reactions have provided new approaches address this challenge. Three major strategies been introduced emerging field: 1) one‐pot in‐situ activation benzoic generate benzoyl hypobromites or hypoiodites; 2) the use specialized photocatalysts like biphenyl/1,4‐dicyanobenzene promote through photo‐induced electron transfer charge processes; 3) LMCT (Ligand‐to‐Metal Charge Transfer) strategy where copper iron salts coordinate carboxylate anion upon visible light excitation. On basis three strategies, review will systematically summarize development visible‐light‐induced decarboxylative functionalization acids, focusing on reaction mechanism substrate scope, discuss their prospects

Язык: Английский

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Furan-Indole-Chromenone-Based Organic Photocatalyst for α-Arylation of Enol Acetate and Free Radical Polymerization Under LED Irradiation

Molecules, Год журнала: 2025, Номер 30(2), С. 265 - 265

Опубликована: Янв. 11, 2025

In this study we report on the efficiency of a furane-indole-chromenone-based organic derivative (FIC) as photocatalyst in α-arylation enol acetate upon LED irradiation at 405 nm, and photoinitiator/photocatalyst free radical polymerization an acrylate group presence bis-(4-tert-butylphenyl)iodonium hexafluorophosphate (Iod) additive, or both Iod ethyl-4-(dimethyl amino) benzoate (EDB) under 365 nm. The photochemical properties new light-sensitive compound are described, wide redox window (3.27 eV) high excited-state potentials FIC*/FIC●− (+2.64 V vs. SCE) FIC●+/FIC* (−2.41 offered by revealed. chemical mechanisms that govern chemistry discussed means different techniques, including fluorescence-quenching experiments, UV-visible absorption fluorescence spectroscopy, cyclic voltammetry analysis.

Язык: Английский

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Three-Coordinate Monomeric Phosphido Complexes of Ni(II)

Inorganic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 20, 2025

This paper reports the synthesis of first series terminal phosphido Ni(II) complexes supported by β-diketiminato ligand [iPrNN] (where iPrNN = 2,4-bis(2,6-diisopropylphenylimido)pentyl). Neutral mononuclear [iPrNN]Ni–PPh2 (2) and [iPrNN]Ni–PAd2 (3) were obtained from reaction [iPrNN]NiBr2Li(thf)2 (1) with R2PM (R Ph, 1-adamantyl (Ad); M Li, K) phosphide reagents. The structures synthesized compounds determined single-crystal X-ray diffraction, which revealed that Ni center in these is three-coordinate an almost planar geometry when R Ph a pyramidal Ad. reactivity was also studied range bond forming reactions, including P–C P–P bonds.

Язык: Английский

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Palladium-Catalyzed Intermolecular 1,3-Dienylation of Propargyl Esters Involving the Insertion of SO₂

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 20, 2025

A palladium-catalyzed three-component 1,3-dienylation of propargylic esters with DABSO and aryl iodides has been developed. This novel reductive cross-coupling reaction produces 2-sufonylated 1,3-dienes as single products in the presence metal Mn high regio- chemoselectivities. Control experiments demonstrated that transformation may undergo a radical process.

Язык: Английский

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Photoredox Radical Cyclization of o-Vinylaryl Isocyanides and Aryldiazonium Tetrafluoroborates for the Synthesis of 2,4-Disubstituted Quinolines

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 23, 2025

Quinolines, a significant part of nitrogen-containing heterocycles, are widely found in functional compounds. Herin, photochemical radical cyclization reaction o-vinylaryl isocyanides and aryldiazonium tetrafluoroborates, has been reported to build 2,4-diaryl quinolines. Readily accessible aryl diazonium salts were utilized as precursors at room temperature. This approach allowed good group tolerance substrate applicability.

Язык: Английский

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