“On-water” defluorinative cyclization of trifluoromethyl enones with phosphine oxides: synthesis of polysubstituted furans

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 3974 - 3981

Published: Jan. 1, 2024

A defluorinative cyclization of readily available trifluoromethyl enones with phosphine oxides for the synthesis polysubstituted furans is developed in a pure water solution.

Language: Английский

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Applications of innovative synthetic strategies in anticancer drug Discovery: The Driving Force of new chemical reactions

Bioorganic & Medicinal Chemistry Letters, Journal Year: 2025, Volume and Issue: 119, P. 130096 - 130096

Published: Jan. 9, 2025

Language: Английский

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Asymmetric synthesis of organophosphorus compounds using H–P reagents derived from chiral alcohols

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(13), P. 2823 - 2846

Published: Jan. 1, 2021

Overview of recent advances in transformations employing optically pure H–P reagents derived from chiral alcohols such as TADDOL, BINOL and menthol the asymmetric synthesis C - P -stereogenic organophosphorus compounds is presented.

Language: Английский

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Recent advances in electrochemical C—H phosphorylation

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

Published: Nov. 3, 2022

The activation of C–H bond, and its direct one-step functionalization, is one the key synthetic methodologies that provides access to a variety practically significant compounds. Particular attention focused on modifications obtained at final stages synthesis complicated molecules, which requires high tolerance presence existing functional groups. Phosphorus an indispensable element life, phosphorus chemistry now experiencing renaissance due new emerging applications in medicinal chemistry, materials (polymers, flame retardants, organic electronics, photonics), agricultural (herbicides, insecticides), catalysis (ligands) other important areas science technology. In this regard, search for new, more selective, low-waste routes become relevant. context, electrosynthesis has proven be eco-efficient convenient approach many respects, where reagents are replaced by electrodes, reactants applied potential determines their “oxidizing or reducing ability”. An electrochemical such processes being developed rapidly demonstrates some advantages over traditional classical methods C-H phosphorylation. main reasons success exclusion excess from reaction system: as oxidants, agents, sometimes metal and/or improvers, challenge isolation, increase wastes reduce yield frequent incompatibility with these Ideal conditions include electron reactant (regulated potential) by-products hydrogen hydrocarbon. review summarizes analyzes achievements preparation various derivatives carbon-phosphorus bonds, collects data redox properties most commonly used precursors. Electrochemically induced reactions both without catalyst metals, competitive oxidation precursors leads either bond generation phosphorus-centered radicals (radical cations) states will examined. focuses publications past 5 years.

Language: Английский

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Defluorophosphorylation of fluoroalkyl peroxides for the synthesis of highly substituted furans

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(5), P. 2000 - 2010

Published: Jan. 1, 2023

A highly tunable defluorophosphorylation of fluorinated peroxides for the preparation C 3,4-diphosphoryl furans and 4-monophosphoryl under conditions with no added transition metals is disclosed.

Language: Английский

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Cobaloxime Catalysis for Enamine Phosphorylation with Hydrogen Evolution

Organic Letters, Journal Year: 2020, Volume and Issue: 22(14), P. 5385 - 5389

Published: June 25, 2020

Direct phosphorylation of enamine and enamide with hydrogen evolution was realized via cobaloxime catalysis under visible-light irradiation. Control experiments spectroscopic studies demonstrated a reductive quenching pathway catalyst to produce phosphinoyl radical, which underwent cross-coupling various enamines (and enamides) give diverse β-phosphinoyl products in good excellent yields. More interestingly, Z/E mixture acyclic could convert into single Z-products reactivity.

Language: Английский

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Electrochemical Phosphorylation of Organic Molecules

The Chemical Record, Journal Year: 2020, Volume and Issue: 20(12), P. 1530 - 1552

Published: Oct. 5, 2020

Abstract Organophosphorus chemistry is a broad field with multi‐dimensional applications in research area of organic, biology, drug design and agrochemicals. Conventional methods have been adopted extensively to access phosphorylated compounds that rely on the use toxic, moisture sensitive phosphorylating agents occur presence oxidants, catalysts, as well high temperatures harsh conditions are required for complete transformations. However, recent progress has made phosphorylation reactions using electricity introduce green sustainable synthetic procedures. These can be performed at mild proceed excellent atom economy. Herein, we targeted electrochemical generation new bonds such C(sp 3 ) −P, 2 O−P, N−P, S−P Se−P. This review aimed offer an overview developments methodology easy organophosphorus electrochemistry.

Language: Английский

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Shining Light on the Light-Bearing Element: A Brief Review of Photomediated C–H Phosphorylation Reactions

Synthesis, Journal Year: 2020, Volume and Issue: 53(06), P. 1003 - 1022

Published: Nov. 23, 2020

Abstract Organophosphorus compounds have numerous useful applications, from versatile ligands and nucleophiles in the case of trivalent organophosphorus species to therapeutics, agrochemicals material additives for pentavalent species. Although phosphorus chemistry is a fairly mature field, construction C–P(V) bonds relies heavily on either prefunctionalized substrates such as alkyl or aryl halides, requires previously oxidized C=N C=O, leading potential sustainability issues when looking at overall synthetic route. In light recent advances photochemistry, using photons reagent can provide better alternatives phosphorylations by unlocking radical mechanisms providing interesting redox pathways. This review will showcase different photomediated phosphorylation procedures available converting C–H into bonds. 1 Introduction 1.1 Compounds 1.2 Phosphorylation: Construction Bonds 1.3 Photochemistry an Alternative Classical Phosphorylations 2 Ionic Mechanisms Involving Nucleophilic Additions 3 Radical Intermediates 3.1 Reactive Carbon Radicals 3.2 Phosphorus 3.2.1 Photoredox: Direct Creation 3.2.2 Indirect 3.2.3 Dual Catalysis 3.3 Photolytic Cleavage 4 Conclusion Outlook

Language: Английский

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Synthesis of 2H-chromenes: recent advances and perspectives

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(48), P. 10530 - 10548

Published: Jan. 1, 2021

As one type of chromene, 2H-chromenes represent important oxygen heterocycles, which not only widely exist in natural products, pharmaceutical agents and biologically relevant molecules, but have also been used broadly materials science organic synthesis. Two major synthetic strategies developed towards such compounds. This review mainly focuses on the recent advances this field, including benzopyran ring formation involving cyclization reactions late-stage functionalization parent 2H-chromenes.

Language: Английский

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Electrocatalytic C–H phosphorylation through nickel(III/IV/II) catalysis

Chem, Journal Year: 2021, Volume and Issue: 7(5), P. 1379 - 1392

Published: May 1, 2021

Language: Английский

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