TMEDA-enabled regioselective sulfenylation of unprotected N-heterocycles via electrochemical sulfinyl radical generation DOI

Qiang Zhong,

Xinru Jiang, Hui Gao

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

An electrochemical sulfenylation of unprotected N -heterocycles with a wide range commercially available arylsulfonyl chlorides was developed.

Language: Английский

Enhancing electrochemical reactions in organic synthesis: the impact of flow chemistry DOI Creative Commons
Morgan Regnier, Clara Vega, Dimitris I. Ioannou

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Utilizing electrons directly offers significant potential for advancing organic synthesis by facilitating novel reactivity and enhancing selectivity under mild conditions. As a result, an increasing number of chemists are exploring electrosynthesis. However, the efficacy electrochemical transformations depends critically on design cell. Batch cells often suffer from limitations such as large inter-electrode distances poor mass transfer, making flow promising alternative. Implementing cells, however, requires foundational understanding microreactor technology. In this review, we briefly outline applications electrosynthesis before providing comprehensive examination existing reactor technologies. Our goal is to equip with insights needed tailor their meet specific requirements effectively. We also highlight application designs in scaling up processes integrating high-throughput experimentation automation. These advancements not only enhance synthetic community but hold promise both academia industry.

Language: Английский

Citations

9

Electrochemical N–H Methylsulfoxidation of Sulfoximines with DMSO DOI Open Access

Qing‐Ru Zhu,

Gen Liu, Yongxiang Wang

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 16, 2025

Comprehensive Summary The N–H methylsulfoxidation of sulfoximines using DMSO as a methylsulfinyl source, induced by electrochemistry, has been developed. This method is the first example an electrochemical reaction in which serves source. Unlike previous reactions involving substrate, exclusively proceed via radical mechanisms, this follows S‐cation pathway. A wide range N ‐methylsulfinyl were successfully obtained.

Language: Английский

Citations

0

Synthesis of Non-C2-Symmetric Biaryldiols via Organo-Electro Catalyzed Aryl–Aryl Dehydrogenative Cross-Coupling DOI
Dingguo Song, Weiwei Huang, Wenji Zhang

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: 147(9), P. 7524 - 7532

Published: Feb. 19, 2025

Despite a few successful examples, controlling the enantioselectivity in asymmetric synthesis of non-C2-symmetric biaryldiols has long been challenging. To address issues and regioselectivity, we introduced novel organoelectrocatalytic strategy enabling aryl-aryl dehydrogenative cross-coupling reactions. Using this approach, valuable were obtained up to 95% yields 97% enantiomeric excesses (ees), these compounds could be further applied as versatile ligands Detailed mechanistic studies supported sequential diradical followed by central-to-axial chirality conversion pathway.

Language: Английский

Citations

0

Electrochemical cobalt-catalyzed semi-deuteration of alkynes to access deuterated Z-alkenes DOI Creative Commons

Wen-Jie Feng,

Zhe Chang, Xi Lu

et al.

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

Published: March 10, 2025

Abstract Deuterium labeling has found extensive applications across various research fields, including organic synthesis, drug design, and molecular imaging. Electrocatalytic semi-hydrogenation of alkynes offers a viable route for the synthesis Z -alkenes, yet it falls short in achieving semi-deuteration these compounds. In this study, we report an electrochemical cobalt-catalyzed transfer deuteration reaction that proficiently accomplishes alkynes, yielding -configuration deuterated alkene products. This utilizes cost-effective cobalt salts as catalysts employs D 2 O AcOD (acetic acid- d ) economical efficient deuterium sources, underscoring its practicality feasibility. The demonstrates broad alkyne substrate scope, high efficiency, good functional group compatibility, excellent -selectivity, remarkable degree rate.

Language: Английский

Citations

0

Supramolecular Engineering of Metal–Organic Membranes with Metal‐Support Interactions for Nanoconfined Synergistic Catalysis DOI

Zihao Zhai,

Junyong Zhu,

Shaochong Cao

et al.

Small Methods, Journal Year: 2025, Volume and Issue: unknown

Published: April 21, 2025

Abstract Continuous‐flow nanoconfined catalysis is crucial for rapid and efficient water purification but challenging traditional reactors. Supramolecular metal–organic membranes, with their intrinsically rich metal nodes, present promising opportunities heterogeneous nano‐catalysis. However, achieving a uniform distribution stabilization of exposed active sites remains challenge. Here, phosphotungstic acid (H 3 PW 12 O 40 : ) modulated interfacial coordination strategy introduced to engineer thin palladium‐1,3,5‐triformylphloroglucinol (Pd‐Tp) nanofilm. The strong electrostatic‐dominated interaction between the fourfold hollow site Pd II enables in situ confined reduction, facilitating enhanced loading cluster‐shaped Pd‐PW nanoparticles within layer. hydrophilic Tp leads competition PdCl 4 2‐ during film formation, giving rise thinner, more hydrophilic, loose‐structured membranes. Importantly, PCM/NaBH system exhibits superior reducibility electron transfer capacity, enabling degradation range organic contaminants, attributed robust metal‐support interactions. PCM achieves rate constant target pollutant 4‐nitrophenol (97.8 ms −1 ), which 175 times faster than that control HCM (0.56 ). This study highlights role microstructure modulation membrane synergistic catalysis.

Language: Английский

Citations

0

N–N Atropisomer Synthesis via Electrolyte- and Base-Free Electrochemical Cobalt-Catalysed C–H Annulation DOI

Jiating Cai,

Linzai Li,

Chuitian Wang

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(23), P. 11524 - 11530

Published: Jan. 1, 2024

An exogenous electrolyte- and base-free electrochemical cobalt-catalysed atroposelective C–H annulation has been established to construct N–N axially chiral isoquinolinones in excellent enantioselectivities good yields.

Language: Английский

Citations

3

Electroreductive Carboxylation of Benzylphosphonium salts with CO2 Through the Cleavage of the C(sp3)-P Bond DOI

Fen Han,

Fenfen Xie,

Mengyun Yin

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(28), P. 5724 - 5728

Published: Jan. 1, 2024

Herein, a novel electroreductive carboxylation of benzylphosphine salts with CO 2 through cleavage the C(sp 3 )-P bond was reported under conditions without redox reagents and noble metal catalysts.

Language: Английский

Citations

2

Wireless asymmetric umpolung electrosynthesis DOI Creative Commons
Sara Grecchi,

Bartlomiej Bonczak,

Filippo Malacarne

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(74), P. 10120 - 10123

Published: Jan. 1, 2024

Electroorganic synthesis has become an exciting tool for the asymmetric conversion of pro-chiral compounds. Herein, we introduced a wireless methodology based on bipolar electrochemistry in synergy with enantioselective capabilities inherently chiral oligomers to induce umpolung chirality transfer. This was exemplified by electro-conversion racemic mixture lansoprazole

Language: Английский

Citations

2

Asymmetric Counteranion‐Directed Electrocatalysis for Enantioselective Control of Radical Cation DOI Open Access

Zhenhui Xu,

Changdi Zheng,

Jie Lin

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 64(1)

Published: Aug. 30, 2024

The control of enantioselectivity in radical cation reactions presents long-standing challenges, despite a few successful examples. We introduce novel strategy asymmetric counteranion-directed electrocatalysis to address chemistry. This concept has been successfully demonstrated two reactions: an dehydrogenative indole-phenol [3+2] coupling and atroposelective C-H/N-H coupling. These have enabled the synthesis benzofuroindolines C-N axially chiral indoles with high yields excellent enantiomeric excesses. Detailed mechanistic studies confirmed radical-radical mechanism. Moreover, density functional theory (DFT) calculations supported indole as pivotal intermediate, rather than neutral indolyl radical, shedding new light on underlying processes driving these reactions.

Language: Английский

Citations

2

Electrochemical synthesis of β-difluoromethylamide compounds by N-benzenesulfonylacrylamide with difluorine reagents DOI

Zhi-Long Lei,

Zong‐Cang Ding,

Shu‐Hui Li

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(59), P. 7614 - 7617

Published: Jan. 1, 2024

A mild and efficient electrochemical method for radical addition, cyclization, migration reaction was described in this work. difluoromethyl produced by anodizing CF

Language: Английский

Citations

1