Electrochemical Oxidative Phosphorylations of Glycine Derivatives with R2P(O)−H‐Containing Compounds via C(sp3)−H Functionalisation DOI

Ruige Wang,

Jie Wang, Yonghong Zhang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(6), P. 900 - 905

Published: Feb. 20, 2023

Herein, we report the development of transition-metal-catalyst- and external-oxidant-free electrochemical cross-coupling hydrogen-evolution chemistry involving glycine amides diarylphosphine oxides. A broad range biologically active α-aminophosphonates was obtained in moderate to good yields a clean sustainable manner. Moreover, TBAB (tetrabutylammonium bromide) electrolyte recycled four times without obvious loss reaction activity. this protocol performed on gram scale under slightly modified electrolytic conditions or combination with continuous flow microreactor technology. Control experiments were used disclose possible free-radical mechanism. As service our authors readers, journal provides supporting information supplied by authors. Such materials are peer reviewed may be re-organized for online delivery, but not copy-edited typeset. Technical support issues arising from (other than missing files) should addressed Please note: The publisher is responsible content functionality any Any queries content) directed corresponding author article.

Language: Английский

TBAI/H2O-cooperative electrocatalytic decarboxylation coupling-annulation of quinoxalin-2(1H)-ones with N-arylglycines DOI
Yuhan Lu,

Zhuo-Tao Zhang,

Hongyu Wu

et al.

Chinese Chemical Letters, Journal Year: 2022, Volume and Issue: 34(7), P. 108036 - 108036

Published: Dec. 5, 2022

Language: Английский

Citations

64

Recent progress on electrochemical synthesis involving carboxylic acids DOI

Na Chen,

Zenghui Ye, Fengzhi Zhang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(25), P. 5501 - 5520

Published: Jan. 1, 2021

Recent progress on sustainable electrochemical synthesis involving carboxylic acids was reviewed.

Language: Английский

Citations

57

The green chemistry paradigm in modern organic synthesis DOI
Sergei G. Zlotin, Ksenia S. Egorova, Valentine P. Ananikov

et al.

Russian Chemical Reviews, Journal Year: 2023, Volume and Issue: 92(12), P. RCR5104 - RCR5104

Published: Dec. 1, 2023

After the appearance of green chemistry concept, which was introduced in vocabulary early 1990s, its main statements have been continuously developed and modified. Currently, there are 10–12 cornerstones that should form basis for an ideal chemical process. This review analyzes accumulated experience achievements towards design products processes reduce or eliminate use generation hazardous substances. The presents views leading Russian scientists specializing various fields this subject, including homogeneous heterogeneous catalysis, fine basic organic synthesis, electrochemistry, polymer chemistry, based on bio-renewable feedstocks energetic compounds materials. A new approach to quantitative evaluation environmental friendliness by authors is described. <br> bibliography includes 1761.

Language: Английский

Citations

39

Electricity-driven asymmetric bromocyclization enabled by chiral phosphate anion phase-transfer catalysis DOI Creative Commons
Xuefeng Tan, Qingli Wang, Jianwei Sun

et al.

Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)

Published: Jan. 23, 2023

Electricity-driven asymmetric catalysis is an emerging powerful tool in organic synthesis. However, induction so far has mainly relied on forming strong bonds with a chiral catalyst. Asymmetry induced by weak interactions catalyst electrochemical medium remains challenging due to compatibility issues related solvent polarity, electrolyte interference, etc. Enabled properly designed phase-transfer strategy, here we have achieved two efficient electricity-driven catalytic bromocyclization processes ion-pairing interaction. The combined use of and phosphate catalyst, together NaBr as the bromine source, constitutes key advantages over conventional chemical oxidation approach. Synergy multiple events, including anodic oxidation, ion exchange, phase transfer, bromination, inhibition Br2 decomposition NaHCO3, proved critical success.

Language: Английский

Citations

36

Electrochemically Mediated Fixation of CO2: Synthesis of Functionalized Oxazolidine‐2,4‐Diones by Three‐Component Reactions DOI
Ting‐Kai Xiong, Qiang Xia,

Xue‐Qi Zhou

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(13), P. 2183 - 2187

Published: June 15, 2023

Abstract Carbon dioxide is a harmful greenhouse gas, as well valuable resource. Here, three‐component cyclization reaction was developed for the synthesis of oxazolidine‐2,4‐diones by immobilizing CO 2 under electrochemistry and copper catalyst. Propargyl amide used substrate to capture carbon produce carboxyl anion, while selenide produced electrophilic receptor activate triple bond electrochemical conditions. Then, intramolecular carried out obtain target product. Through this environmentally friendly strategy, series important synthesized.

Language: Английский

Citations

32

Manganese-Mediated Electrochemical Oxidation of Thioethers to Sulfoxides Using Water as the Source of Oxygen Atoms DOI
Md Asmaul Hoque,

Tianxiao Jiang,

Darren L. Poole

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(31), P. 21960 - 21967

Published: July 23, 2024

Oxygen-atom transfer reactions are a prominent class of synthetic redox that often use high-energy oxygen-atom donor reagents. Electrochemical methods can bypass these reagents by using water as the source oxygen atoms through pathways involving direct or indirect (mediated) electrolysis. Here, manganese porphyrins and related mediators shown to be effective molecular electrocatalysts for selective oxidation thioethers sulfoxides, without overoxidation sulfone. The proceed proton-coupled Mn

Language: Английский

Citations

12

Electrochemical Oxidative Dearomatization of Electron-deficient Phenols Using Br+/Br Catalysis DOI Creative Commons

Kai Matsui,

Muhammet Uyanik, Kazuaki Ishihara

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

An electrochemical method for oxidative dearomatization of electron-deficient phenols is reported, using tetrabutylammonium bromide as a catalytic mediator under aqueous biphasic conditions.

Language: Английский

Citations

1

Electrochemical Oxidative Halogenation of N-Aryl Alkynamides for the Synthesis of Spiro[4.5]trienones DOI

Ke Yu,

Xianqiang Kong,

Jiajun Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 86(1), P. 917 - 928

Published: Dec. 7, 2020

We developed a green method for the synthesis of spiro[4.5]trienones through an electrochemical oxidative halocyclization with N-aryl alkynamides. This reaction was conducted under metal-catalyst- and exogenous-oxidant-free conditions at room temperature. Using readily available LiCl, LiBr, LiI as halogen source, variety dearomative halo-spirocyclization products were obtained in good to excellent yields broad scope functional group tolerance.

Language: Английский

Citations

61

Electrohalogenation of organic compounds DOI
Marcos R. Scheide, Celso R. Nicoleti, Guilherme M. Martins

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(12), P. 2578 - 2602

Published: Jan. 1, 2021

In this review we target sp, sp2and sp3carbon fluorination, chlorination, bromination and iodination reactions using electrolysis as a redox medium. Mechanistic insights substrate reactivity are also discussed.

Language: Английский

Citations

55

Electrochemical C-H Halogenations of Enaminones and Electron-Rich Arenes with Sodium Halide (NaX) as Halogen Source for the Synthesis of 3-Halochromones and Haloarenes DOI
Yan Lin, Jun Jin, Chaoli Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(17), P. 12378 - 12385

Published: Aug. 16, 2021

Without employing an external oxidant, the simple synthesis of 3-halochromones and various halogenated electron-rich arenes has been realized with electrode oxidation by simplest sodium halide (NaX, X = Cl, Br, I) as halogen source. This electrochemical method is advantageous for mild room temperature operation, environmental friendliness well broad substrate scope in both C–H bond donor source components.

Language: Английский

Citations

55