Redox-neutral and metal-free synthesis of 3-(arylmethyl)chroman-4-ones via visible-light-driven alkene acylarylation DOI Creative Commons
Yan Ding,

Shengjiao Yu,

Man Ren

et al.

Frontiers in Chemistry, Journal Year: 2022, Volume and Issue: 10

Published: Oct. 31, 2022

A metal- and aldehyde-free visible-light-driven photoredox-neutral alkene acylarylation with readily available cyanoarenes is described. variety of 3-(arylmethyl)chroman-4-ones (i.e., homoisoflavonoids) analogs are efficiently synthesized good functional group tolerance. This mild protocol relies on a phosphoranyl radical-mediated acyl radical-initiated cyclization selective radical-radical coupling sequence, also further highlighted by subsequent derivatization to chromone 2H-chromene as well its application in the three-component acylarylation.

Language: Английский

Photosynthesis of 3-Alkylated Coumarins from Carboxylic Acids Catalyzed by a Na2S-Based Electron Donor–Acceptor Complex DOI

Hai‐Yang Song,

Meiyi Liu,

Jing Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(4), P. 2288 - 2295

Published: Feb. 4, 2023

A simple and practical electron donor-acceptor (EDA) strategy to synthesize various 3-alkylated coumarins from easily available naturally abundant carboxylic acids under photocatalyst-, oxidant-, additive-free mild conditions is reported. Using Na2S as the catalytic donor, a series of primary, secondary, tertiary carbon radicals can be efficiently generated, EDA complex regenerated without an alkaline additive.

Language: Английский

Citations

31

Substituent-Controlled Regioselective Photoinduced Cyclization of N-Allylbenzamides with N-Sulfonylaminopyridinium Salts DOI
Changduo Pan,

Zixian Yang,

Xian Wu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(3), P. 494 - 499

Published: Jan. 12, 2023

The annulation reactions of N-allylbenzamides with N-sulfonylaminopyridinium salts were developed under metal-free photoinduced mild conditions. Substituent-controlled sulfonaminoarylation and sulfonaminooxylation benzamides realized: lead to benzosultams, while N-(2-phenylallyl)benzamides give sulfonamidylated oxazoline derivatives. Control experiments indicated that those undergo a radical pathway arylsulfonamidyl radicals as the intermediates. aryl C–H bond functionalization in was involved for first time benzosultams.

Language: Английский

Citations

24

Selective Electrochemical Modification and Degradation of Polymers DOI
Rhys W. Hughes, J. Márquez, James B. Young

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(20)

Published: Feb. 28, 2024

Abstract We demonstrate that electrochemical‐induced decarboxylation enables reliable post‐polymerization modification and degradation of polymers. Polymers containing N ‐(acryloxy)phthalimides were subjected to electrochemical under mild conditions, which led the formation transient alkyl radicals. By installing these redox‐active units, we systematically modified pendent groups chain ends polyacrylates. This approach enabled production poly(ethylene‐ co ‐methyl acrylate) poly(propylene‐ copolymers, are difficult synthesize by direct polymerization. Spectroscopic chromatographic techniques reveal transformations near‐quantitative on several polymer systems. Electrochemical also all‐methacrylate poly( ‐(methacryloxy)phthalimide‐ methacrylate) copolymers with a efficiency >95 %. Chain cleavage is achieved through ‐hydroxyphthalimide ester subsequent β‐scission backbone radical. Electrochemistry thus shown be powerful tool in selective controlled macromolecular degradation.

Language: Английский

Citations

14

Self-assembled nanodrug based on ferroptosis inducer and sonosensitizer for enhanced sonodynamic-triggered multimodal synergistic therapy of prostate cancer DOI
Yushuai Wu, Ruirui Zhao, Xiao Wu

et al.

European Journal of Pharmaceutics and Biopharmaceutics, Journal Year: 2025, Volume and Issue: 208, P. 114656 - 114656

Published: Feb. 3, 2025

Language: Английский

Citations

1

Advances in the Application of Acetonitrile in Organic Synthesis since 2018 DOI Open Access
Pinyong Zhong, Linjun Zhang, Nianhua Luo

et al.

Catalysts, Journal Year: 2023, Volume and Issue: 13(4), P. 761 - 761

Published: April 16, 2023

Acetonitrile is commonly used as an organic solvent and can also be important intermediate in synthesis. Its widespread use has led to the development of new methods for synthesis a variety compounds. In past decades, conversion reactions acetonitrile building block have become one most-attractive fields Especially field electrochemical conversions involving acetonitrile, due its good conductivity environmentally friendly features, it powerful compelling tool afford nitrogen-containing compounds or nitrile-containing this review, we mainly discuss research progress five years, covering both conventional Besides, detailed discussion substrate scope mechanistic pathways provided.

Language: Английский

Citations

21

The Interaction Mechanism of Picolinamide Fungicide Targeting on the Cytochrome bc1 Complex and Its Structural Modification DOI
Ying Dong, Bo Li,

Mao-Xue Yin

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(7), P. 3755 - 3762

Published: Feb. 12, 2024

Picolinamide fungicides, structurally related to UK-2A and antimycin-A, bind into the Qi-site in bc1 complex. However, detailed binding mode of picolinamide fungicides remains unknown. In present study, antimycin-A were selected study inhibitors with four protonation states by integrating molecular dynamics simulation, docking, mechanics Generalized Born surface area (MM/GBSA) calculations. Subsequently, a series new derivatives designed synthesized further understand effects substituents on tail phenyl ring. The computational results indicated that substituted aromatic rings pharmacophore fragments made primary contribution when bound protein. Compound 9g-hydrolysis formed H-bonds Hie201 Ash228 showed an IC50 value 6.05 ± 0.24 μM against porcine 9c, simpler chemical structure, higher control than florylpicoxamid cucumber downy mildew expanded fungicidal spectrum fungicides. structural mechanistic insights obtained from will provide valuable clue for future designing promising inhibitors.

Language: Английский

Citations

5

Structure-Based Discovery of New Succinate Dehydrogenase Inhibitors via Scaffold Hopping Strategy DOI

Yuan-Hui Huang,

Ge Wei,

Wenjie Wang

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2023, Volume and Issue: 71(47), P. 18292 - 18300

Published: Sept. 22, 2023

Scaffold hopping strategy has become one of the most successful methods in process molecular design. Seeking to develop novel succinate dehydrogenase inhibitors (SDHIs), we employed a scaffold design compounds featuring geminate dichloralkenes (gem-dichloralkenes) fragment. After stepwise modifications, series N-cyclopropyl-dichloralkenes-pyrazole-carboxamide derivatives was synthesized. Among them, G28 (IC50 = 26.00 nM) and G40 27.00 were identified as best inhibitory activity against porcine SDH, with IC50 values reaching nanomolar range, outperforming lead compound pydiflumetofen. Additionally, greenhouse assay indicated that G37 (EC90 0.031 mg/L) G34 1.67 displayed extremely high activities wheat powdery mildew (WPM) cucumber (CPM), respectively. Computational results further revealed gem-dichloralkene fragment fluorine substituted pyrazole form an extra hydrophobic interaction dipolar-dipolar SDH. In summary, our study provides outstanding fungicidal properties, obtained through hopping, holds great potential for future research on PM control.

Language: Английский

Citations

13

Photoredox-Catalyzed Redox-Neutral Decarboxylative C–H Acylations of Coumarins with α-Keto Acid DOI
Bin Sun, Yingying Wang, Jia‐Yin Wang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(14), P. 2466 - 2470

Published: March 31, 2023

A novel and green photocatalytic strategy for the synthesis of C-4-acylated coumarins with α-keto acids 3-nitrocoumarin has been developed. This operationally simple protocol works under mild reaction conditions, providing convenient access to 4-acyl coumarin derivatives. The control experimental results showed that nitro radical produced by cleavage C-N bond acts as an electron acceptor complete cycle, achieving a redox-neutral reaction.

Language: Английский

Citations

11

Efficient Synthesis of Nitrile Compounds through Amide Conversion via N-Boroamide Intermediates DOI
Yang Li, Yanan Dong, Yuehui Li

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(2), P. 638 - 638

Published: Jan. 1, 2024

Language: Английский

Citations

2

Photoredox-Catalyzed Tandem Radical Cyclization/Hydroxylation for the Synthesis of 4-Hydroxyalkyl-3,3-difluoro-γ-lactams DOI
Bin Sun,

Xiaohui Zhuang,

Jieli Yin

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 14177 - 14185

Published: Sept. 29, 2022

The photoredox-catalyzed radical difluoroalkylation/cyclization/hydroxylation cascade reaction of various 2-bromo-2,2-difluoro-N-arylacetamides containing unactivated alkene moieties has been developed, providing green and efficient access to 4-hydroxyalkyl-3,3-difluoro-γ-lactams. Control experiments confirmed a process, inexpensive air acted as the sole hydroxy resource. In addition, highlights this protocol include good tolerance for variety functional groups, lower photocatalyst loading, ease operation.

Language: Английский

Citations

11