Recent advances in the electrochemical synthesis of organophosphorus compounds

Beilstein Journal of Organic Chemistry, Год журнала: 2025, Номер 21, С. 770 - 797

Опубликована: Апрель 16, 2025

In this review, we describe recent advances in electrochemical green methods for the synthesis of various organophosphorus compounds through formation phosphorus–carbon, phosphorus–nitrogen, phosphorus–oxygen, phosphorus–sulfur, and phosphorus–selenium bonds. The impact different electrodes is also discussed matter. Graphite, platinum, RVC, nickel have been used extensively compounds. made method a promising preparing structures. This review an introduction to encourage scientists use electrosynthesis as green, precise, low-cost prepare phosphorous

Язык: Английский

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Heterocyclic Electrochemistry: Renewable Electricity in the Construction of Heterocycles

ACS Omega, Год журнала: 2023, Номер 8(7), С. 6175 - 6217

Опубликована: Фев. 1, 2023

Numerous applications in the realm of biological exploration and drug synthesis can be found heterocyclic chemistry, which is a vast subject. Many efforts have been developed to further improve reaction conditions access this interesting family prevent employing hazardous ingredients. In instance, it has stated that green environmentally friendly manufacturing methodologies introduced create N-, S-, O-heterocycles. It appears one most promising methods these types compounds avoiding use stoichiometric amounts oxidizing/reducing species or precious metal catalysts, only catalytic are sufficient, represent an ideal way contributing toward resource economy. Thus, renewable electricity provides clean electrons (oxidant/reductant) initiate cascade via producing reactive intermediates facilitate building new bonds for valuable chemical transformations. Moreover, electrochemical activation using metals as mediators identified more efficient strategy selective functionalization. indirect electrolysis makes potential range practical, less side reactions occur. The latest developments electrolytic O-heterocycles main topic mini review, was documented over last five years.

Язык: Английский

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Cp₂Fe Mediated Electrochemical Synthesis of Phosphonylated Spirocyclic Indolines via Dearomatization of Indoles

Organic Letters, Год журнала: 2023, Номер 25(21), С. 3956 - 3960

Опубликована: Май 18, 2023

A general and robust strategy for the synthesis of phosphonylated spirocyclic indolines has been developed through Cp2Fe-catalyzed electrochemical dearomaztizaion indoles, which proven challenging to achieve via chemical oxidants. range 3,3-spiroindolines were obtained in moderate good yields with excellent diastereoselectivities. The synthetic application was further illustrated by its easy scalability antitumor activity product.

Язык: Английский

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

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(6), С. 900 - 905

Опубликована: Фев. 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.

Язык: Английский

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Electrochemical oxidative N–H/P–H cross-coupling with H₂ evolution towards the synthesis of tertiary phosphines

Chemical Science, Год журнала: 2022, Номер 13(10), С. 3002 - 3008

Опубликована: Янв. 1, 2022

Tertiary phosphines(iii) find widespread use in many aspects of synthetic organic chemistry. Herein, we developed a facile and novel electrochemical oxidative N-H/P-H cross-coupling method, leading to series expected tertiary under mild conditions with excellent yields. It is worth noting that this protocol features very good reaction selectivity, where only 1 : ratio amine phosphine was required the reaction. Moreover, proved be practical scalable. Mechanistic insights suggested P radical involved

Язык: Английский

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C−H Bond Functionalization under Electrochemical Flow Conditions

The Chemical Record, Год журнала: 2022, Номер 22(6)

Опубликована: Март 22, 2022

Abstract Electrochemical C−H functionalization is a rapidly growing area of interest in organic synthesis. To achieve maximum atom economy, the flow electrolysis process more sustainable. This allows shorter reaction times, safer working environments, and better selectivities. Using this technology, problem overoxidation can be reduced less emergence side products or no are possible. Flow electro‐reactors provide high surface‐to‐volume ratios contain electrodes that closely spaced where diffusion layers overlap to give desired product, electrochemical processes now managed without need for deliberately added supporting electrolyte. Considering importance functionalization, comprehensive review presented. Herein, we summarize construction C−C C−X (X=O, N, S, I) bonds formation. Also, benzylic oxidation access biologically active molecules discussed.

Язык: Английский

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Ultrasound-assisted synthesis of pyrimidines and their fused derivatives: A review

Ultrasonics Sonochemistry, Год журнала: 2021, Номер 79, С. 105683 - 105683

Опубликована: Июль 27, 2021

The pyrimidine scaffold is present in many bioactive drugs; therefore, efficient synthetic routes that provide shorter reaction times, higher yields, and site-selective reactions are constantly being sought. Ultrasound (US) irradiation has emerged as an alternative energy source the synthesis of these heterocyclic scaffolds, over last ten years there been a significant increase number publications mentioning US either construction or derivatization core. This review presents detailed summary (with 140 references) effects (synergic not) on core through classical (e.g., multicomponent, cyclocondensation, cycloaddition, alkylation reactions). main points were taken into consideration follows: chemo- regioselectivity issues, results conventional heating methods compared to mechanistic insights also presented discussed for key reactions.

Язык: Английский

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Electrochemically driven regioselective C−H phosphorylation of group 8 metallocenes

Nature Communications, Год журнала: 2022, Номер 13(1)

Опубликована: Июнь 17, 2022

Abstract Metallocenes are privileged backbones for synthesis and catalysis. However, the direct dehydrogenative C−H functionalization of unsymmetric metallocenes suffers from reactivity selectivity issues. Herein, we report an electrochemically driven regioselective phosphorylation group 8 metallocenes. Mechanistic investigations indicate this cross coupling occurs through electrophilic radical substitution metallocene with a phosphoryl radical, facilitated by itself. This work not only offers efficient divergent phosphorylated metallocenes, but also provides guide to interpret regioselectivity

Язык: Английский

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Electrochemical Oxidation‐Induced Oxyphosphorylation of Alkenes and Alkynes with Water via Hydrogen Atom Transfer

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(16), С. 2735 - 2740

Опубликована: Июль 1, 2022

Abstract A metal‐ and exogenous‐oxidant‐free oxidation‐induced oxyphosphorylation of alkenes alkynes with water for β‐ketophosphonates has been developed through the radical coupling under electrochemical conditions. This protocol is compatible a wide range alkenes, alkynes, diarylphosphorus derivatives, enables gram‐scale synthesis β‐ketophosphonates. The mechanistic study revealed that P radicals were generated via hydrogen atom transfer (HAT) event jointly mediated by tetrabutylammonium acetate anode oxidation process. magnified image

Язык: Английский

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Arenes and Heteroarenes C−H Functionalization Under Enabling Conditions: Electrochemistry, Photoelectrochemistry & Flow Technology

The Chemical Record, Год журнала: 2023, Номер 23(10)

Опубликована: Май 31, 2023

Abstract C−H bond functionalization generates molecular complexity in single‐step transformation. However, the activation of bonds requires expensive metals or stoichiometric amounts oxidizing/reducing species. In many cases, they often require pre‐functionalization starting molecules. Such pre‐activating measures cause waste generation and their separation from final product is also troublesome. such a scenario, reactions activating elements generating renewable energy resources as electricity light would be more efficient, green, cost‐effective. Further, incorporation growing flow technology chemical transformation processes will accelerate safer accesses valuable products. Arenes & heteroarenes are ubiquitous pharmaceuticals, natural products, medicinal compounds, other biologically important Herein, we discussed enabling tools technologies used for recent arenes heteroarenes.

Язык: Английский

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