Visible Light Photoredox Catalysis in the Synthesis of Phosphonate-Substituted 1,10-Phenanthrolines DOI Creative Commons
Gleb V. Morozkov,

Artem A. Troickiy,

Alexei D. Averin

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(23), P. 5558 - 5558

Published: Nov. 25, 2024

Photoredox-catalyzed phosphonylation of bromo-substituted 1,10-phenanthrolines under visible light irradiation was studied. The reaction shown to proceed mild conditions with Eosin Y as a photocatalyst in DMSO blue irradiation. It is transition-metal-free and affords the target phosphonate-substituted moderate yields (26-51%) 22 40 h. rate selectivity depend largely on position bromine atom, well nature other substituents 1,10-phenanthroline core.

Language: Английский

Electroreduction strategy: a sustainable tool for the generation of aryl radicals DOI
Xiaoqing Xie,

Wei Zhou,

Ruchun Yang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4318 - 4342

Published: Jan. 1, 2024

This review primarily focuses on the generation of aryl radicals via an electroreduction strategy, and systematically elaborates synthetic applications, scope, limitations substrates.

Language: Английский

Citations

9

Dearomative 1,4-Difunctionalization of Non-Activated Arenes Enabled by Boryl Radical-Mediated Halogen-Atom Transfer DOI
Chengliang Deng, Hao Wu,

Sheng Li

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 1294 - 1304

Published: Jan. 7, 2025

Given the widespread presence of spirocyclic scaffolds in natural products and pharmacologically relevant synthetic compounds, development efficient methodologies for their construction holds great importance medicinal chemistry pharmaceutical research. In this study, a general photochemical dearomative spirocyclization nonactivated arenes has been established. The key to method lies ability amine-borane radicals activate aryl bromides iodides via halogen-atom transfer, thereby allowing conversion halides into corresponding subsequent chemodivergent transformations. remarkable compatibility versatility 1,4-difunctionalization is showed by rapid assembly structurally diverse 1,4-cyclohexadiene-based spirocycles incorporating oxindole, indoline, or dihydrobenzofuran subunits. Moreover, potential utility protocol exemplified formal total synthesis vasopressin V2 receptor antagonist Satavaptan.

Language: Английский

Citations

1

The Strategies towards Electrochemical Generation of Aryl Radicals DOI
Xiaobao Zeng

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: July 16, 2024

The advancement in electrochemical techniques has unlocked a new path for achieving unprecedented oxidations and reductions of aryl radical precursors controlled selective manner. This approach facilitates the construction aromatic carbon-carbon carbon-heteroatom bonds. In light green merits growing importance this technique chemistry, review aims to provide an overview recent advance generation radicals organized by precursor type, with focus on substrate scope, limitation, underlying mechanism, thereby inspiring future work generation.

Language: Английский

Citations

8

Direct C(sp3)-H functionalization with aryl and alkyl radicals as intermolecular hydrogen atom transfer (HAT) agents DOI
Jia‐Lin Tu, Binbin Huang

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

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

Language: Английский

Citations

6

Light‐Induced Direct Decarboxylative Functionalization of Aromatic Carboxylic Acids DOI Open Access
Jia‐Lin Tu, Zhengjia Shen, Binbin Huang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(21), P. 4263 - 4273

Published: Aug. 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

Language: Английский

Citations

4

Palladium-Catalyzed Transfer Iodination from Aryl Iodides to Nonactivated C(sp3)–H Bonds DOI
Emilien Le Saux, Bill Morandi

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 4, 2025

We report a new strategy for the catalytic iodination of nonactivated C(sp3)-H bonds. The method merges concepts shuttle and light-enabled palladium catalysis to employ aryl iodides as both hydrogen atom transfer reagents iodine donors. A noncanonical Pd0/PdI cycle is harnessed from C(sp2) bond under mild conditions, which tolerate sensitive functional groups. This mechanism also applied implement thiolation that exploits reversible steps system.

Language: Английский

Citations

0

Water Effect on the Photochemistry of Arylazo Sulfonates DOI Creative Commons
Luca Nicchio, Hawraz Ibrahim M. Amin,

Stefano Genualdo

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 30, 2025

The effect of water on visible-light-driven generation aryl radicals or cations from colored shelf-stable arylazo sulfonates has been investigated. Photoinduced ionic and radical decomposition these salts compete, depending the media used. In organic solvents, light-induced homolysis N-S bond occurs, resulting may be used to some extent for arylation reactions. On contrary, in neat water, chemistry is prevented by an efficient photoheterolysis, a reactive cation otherwise generated.

Language: Английский

Citations

0

Regioselective 1,2-Di(hetero)arylation of Activated and Unactivated Alkenes with (Hetero)aryl Chlorides DOI

Yingjun Lan,

Siqi Xie, Bin Liu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 1, 2025

Aryl chlorides are more commercially available and lower cost compared with aryl bromides iodides. However, the use of (hetero)aryl as radical precursors for di(hetero)arylation alkenes remains an underdeveloped area. Furthermore, existing examples theses reactions predominantly confined to activated alkenes. In this study, we introduce a photoirradiation-promoted benzophenone-catalyzed 1,2-di(hetero)arylation process that is applicable both unactivated alkenes, utilizing cyanoarenes sources. Importantly, method allows simultaneous introduction two heterocycles high regioselectivity.

Language: Английский

Citations

0

Electrochemically Driven Denitrative Cyanation of Nitroarenes DOI
Yiyi Chen,

Qisheng Chen,

Shuangquan Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7555 - 7559

Published: Sept. 3, 2024

A practical denitrative cyanation of feedstock nitroarenes under mild and transition metal-free reaction conditions has been developed. The key to success lies in the use electrochemically driven, inexpensive ionic liquid

Language: Английский

Citations

1

Chemoselective Approach to Versatile Acyl Fluorides by Photoinduced Activation of p-Methoxybenzyl Esters DOI

Hee-Chan Jeong,

Hyo‐Jun Lee, Keiji Maruoka

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(37), P. 7956 - 7960

Published: Sept. 11, 2024

A new strategy for the metal-free photoinduced activation of

Language: Английский

Citations

1