Cited by Detailed Studies on the Methoxylation and Subsequent Dealkylation of N,N-Diethylbenzenesulfonamide Using a Tailor-Made Electrosynthetic Reactor

Electrochemical Sulfonylation/Cyclization of N-Alkenylacrylamides with Sodium Sulfinates or Sulfonyl Hydrazides DOI

Zhixian Yang,

Lu-Cai Ding,

Gui-Hong Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10660 - 10677

Published: July 18, 2024

Two general protocols for the regioselective electrochemically enabled sulfonylation cyclization of

Language: Английский

Citations

Photo-mediated radical relay oximinosulfonamidation of alkenes with N-nitrosamines triggered by DABSO DOI

Ji‐Wei Sang,

Hong Chen, Yu Zhang

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(13), P. 7849 - 7856

Published: Jan. 1, 2024

N -Nitrosamines represent a class of bifunctional nitrogen-radical precursors, but their application potential remains largely unexplored.

Language: Английский

Citations

Development of N-centered radical scavengers that enables photoredox-catalyzed transition-metal-free radical amination of alkyl pinacol boronates DOI

Changlei Zhu, Jiaxin Lin, Xiaoguang Bao

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: April 4, 2025

In recent years, amination of alkylboronates through ionic copper catalysis or boron-ate complex 1,2-metalation has been well established, but complementary radical processes remain less studied before. Herein, based on rational design, we develop several imine-type N-centered scavengers and apply them to the alkylboronates. The reaction proceeds under mild photoredox-catalyzed transition-metal-free conditions features excellent functional group tolerance. It also enables preparation a range medicinally valuable amine derivatives from natural products. Further application this reagent in C-H amination, deoxygenative decarboxylative three component trifluoromethylative/sulfonylative aminations are realized. mechanistic studies DFT calculations conducted provide detailed evidence for mechanism.

Language: Английский

Citations

Difunctionalization of gem-difluoroalkenes for amination and heteroarylation via metal-free photocatalysis DOI

Yuanchen Zhong,

Zhen Zhuang,

Xiaofei Zhang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(36), P. 4830 - 4833

Published: Jan. 1, 2024

Herein we report a metal-free photocatalytic method for amination and heteroarylation of gem -difluoroalkenes.

Language: Английский

Citations

Photocatalytic Synthesis and Functionalization of Sulfones, Sulfonamides and Sulfoximines DOI

José J. Garrido‐González, Katy Medrano‐Uribe, Cristian Rosso

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(44)

Published: July 22, 2024

Sulfur(VI)-based functional groups are popular scaffolds in a wide variety of research fields including synthetic and medicinal chemistry, as well chemical biology. The growing interest sulfur(VI)-containing molecules has motivated the scientific community to explore new methods synthesize modify them. Here, photocatalysis plays key role granting access types reactivity under mild reaction conditions. In this Perspective, we present selection works reported last six years focused on photocatalytic assembly sulfones, sulfonamides, sulfoximines. We addressed intermediates for each transformation, while discussing limitations strength points protocols. Future directions field finally presented.

Language: Английский

Citations

Photoinduced EnT-Mediated Sulfonamidylimination of Alkenes and (Hetero)arenes with Iminophenylacetic Acids Oxime Esters DOI

Zetian Sun,

Jianting Zhang, Xiaohua Du

et al.

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

Published: Jan. 1, 2024

Sulfonamidyl radicals are generated via photoinduced EnT and applied for the diamination of alkenes (hetero)arenes.

Language: Английский

Citations

DABCO‐Mediated Photoelectrochemical Three‐Component Sulfonocyclization of 3‐Aza‐1,5‐dienes DOI

Lu-Cai Ding,

Gui-Hong Yang,

Li Luo

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 2, 2024

Comprehensive Summary Herein, we report a rare example of three‐component net‐oxidative sulfonylation SO 2 surrogate with an oxidatively activated radical precursor under mild and metal‐ external‐oxidant‐free conditions. The mildness sustainability the reaction are enabled by photoelectrocatalysis, 3‐aza‐1,5‐dienes, organotrifluoroborates 1,4‐diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) undergo sulfonylative cyclization to afford sulfono 4‐pyrrolin‐2‐ones in atom‐economical manner broad substrate scope good functional‐group tolerance. protocol is amenable late‐stage diversification complex molecular architectures as well gram‐scale synthesis. Sunlight could be used light source, conducted all‐solar mode using commercially available photovoltaic panel generate electricity situ . Mechanistic studies reveal that generated (DABCO), which was generally innocent previous reactions, functions electron shuttle between photocatalytic cycle reactants.

Language: Английский

Citations

Metal-free introduction of primary sulfonamide into electron-rich aromatics DOI

Ming‐Ming Wang, Kai Johnsson

Chemical Science, Journal Year: 2024, Volume and Issue: 15(31), P. 12310 - 12315

Published: Jan. 1, 2024

Inspired by the Burgess reagent, we report a mild and practical synthesis of primary sulfonamides from electron-rich aromatic compounds using in situ formed N -sulfonylamine as electrophile.

Language: Английский

Citations

Novel heterocyclic amide derivatives containing a diphenylmethyl moiety: systematic optimizations, synthesis, antifungal activity and action mechanism DOI

Feng Peng,

Jianqi Chai,

Yue Xie

et al.

Pest Management Science, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 30, 2024

Abstract BACKGROUND The development of fungicides with low cross resistance, high efficacy and resistance plays a central role in protecting crops, reducing yield losses, improving quality maintaining global food security. Based on this important role, after systematic optimization strategy, novel heterocyclic amide derivatives bearing diphenylmethyl fragment were screened, synthesized verified the spectrographic x‐ray diffraction analysis. RESULTS In study, aforementioned obtained compound B19 that was measured for antifungal activity against Rhizoctonia solani (median effective concentration, EC 50 = 1.11 μg mL −1 ). Meanwhile, anti‐ R. protective effect (79.34%) evaluated vivo at 100 , which is comparable to control agent fluxapyroxad (80.67%). Thence, morphological observations revealed induced mycelium disruption shrinking, mitochondrial number reduction apoptosis acceleration, consistent results membrane potential cell permeability. Further investigations found target enzyme SDH, exerted fluorescence quenching dynamic curves similar commercialized SDHI fluxapyroxad. Additionally, research by molecular docking MD simulations demonstrated had binding mode acting surrounding residues SDH active pocket offluxapyroxad. CONCLUSION above containing moiety are promising scaffolds targeting fungi provide valuable leads develop new inhibitors. © 2024 Society Chemical Industry.

Language: Английский

Citations

Conversion of Carboxylic Acids to Sulfonamide Bioisosteres via Energy Transfer Photocatalysis DOI

Zhipeng Zong,

H. J. Yang,

Lulu Yuan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 1, 2024

More than 450 drugs containing a carboxylic acid functional group have been marketed worldwide. Herein, we report concise and environmentally friendly organic photoinduced protocol for the interconversion of acids into their bioisosteres. With this strategy, variety substrates, including alkyl, (hetero)aryl, alkenyl acids, as well various biologically relevant are successfully converted primary sulfonamides.

Language: Английский

Citations