A Practical and Scalable Approach to Fluoro‐Substituted Bicyclo[1.1.1]pentanes

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(29)

Published: May 31, 2022

After more than 20 years of trials, a practical scalable approach to fluoro-substituted bicyclo[1.1.1]pentanes (F-BCPs) has been developed. The physicochemical properties the F-BCPs have studied, and core was incorporated into structure anti-inflammatory drug Flurbiprofen in place fluorophenyl ring.

Language: Английский

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Transition metals-catalyzed amination of biomass feedstocks for sustainable construction of N-heterocycles

Coordination Chemistry Reviews, Journal Year: 2023, Volume and Issue: 502, P. 215622 - 215622

Published: Dec. 26, 2023

Language: Английский

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Radical-Polar Crossover Enabled Triple Cleavage of CF₂Br₂: A Multicomponent Tandem Cyclization to 3-Fluoropyrazoles

Organic Letters, Journal Year: 2023, Volume and Issue: 25(32), P. 6062 - 6066

Published: Aug. 8, 2023

The elaboration of step-economy and catalytic approaches for accessing diverse fluorinated heterocyclics is highly desirable. Described herein a radical-polar crossover enabled three-component cyclization to polysubstituted fluoropyrazoles by using CF2Br2 as novel C1F1 synthon. Mechanistic experiments revealed that the in situ generation reactive intermediate gem-difluorovinylimine ion key this transformation. This protocol unlocks reactivity adds significant synthetic values fluorine chemistry.

Language: Английский

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Copper-Catalyzed Cross-Coupling of Benzylic C–H Bonds and Azoles with Controlled N-Site Selectivity

Journal of the American Chemical Society, Journal Year: 2021, Volume and Issue: 143(36), P. 14438 - 14444

Published: Aug. 31, 2021

Azoles are important motifs in medicinal chemistry, and elaboration of their structures via direct N-H/C-H coupling could have broad utility drug discovery. The ambident reactivity many azoles, however, presents significant selectivity challenges. Here, we report a copper-catalyzed method that achieves site-selective cross-coupling pyrazoles other N-H heterocycles with substrates bearing (hetero)benzylic C-H bonds. Excellent

Language: Английский

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Trifluoromethylated Pyrazoles via Sequential (3 + 2)-Cycloaddition of Fluorinated Nitrile Imines with Chalcones and Solvent-Dependent Deacylative Oxidation Reactions

Organic Letters, Journal Year: 2022, Volume and Issue: 24(13), P. 2499 - 2503

Published: March 28, 2022

A general approach for preparation of two types polyfunctionalized 3-trifluoromethylpyrazoles is reported. The protocol comprises (3 + 2)-cycloaddition the in situ generated trifluoroacetonitrile imines with enones leading to trans-configured 5-acyl-pyrazolines a fully regio- and diastereoselective manner. Initially formed cycloadducts were aromatized by treatment manganese dioxide. Depending on solvent used, oxidation step either led substituted pyrazoles (DMSO) or proceeded via deacylative pathway afford 1,3,4-trisubstituted derivatives (hexane) excellent selectivity.

Language: Английский

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Impact of per- and polyfluorinated alkyl substances (PFAS) on the marine environment: Raising awareness, challenges, legislation, and mitigation approaches under the One Health concept

Marine Pollution Bulletin, Journal Year: 2023, Volume and Issue: 194, P. 115309 - 115309

Published: Aug. 15, 2023

Per- and polyfluorinated alkyl substances (PFAS) have long been known for their detrimental effects on the ecosystems living organisms; however long-term impact marine environment is still insufficiently recognized. Based PFAS persistence bioaccumulation in complex food network, adverse will be exacerbated by global processes such as climate change synergies with other pollutants, like microplastics. The range of fluorochemicals currently included umbrella has significantly expanded due to updated OECD definition, raising new concerns about poorly understood dynamics negative ocean wildlife human health. Mitigation challenges approaches, including biodegradation studied materials environmental removal are proposed here, highlighting importance ongoing monitoring bridging research gaps. EU regulations, good practices legal frameworks discussed, emphasis recommendations improving ecosystem management.

Language: Английский

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Chemo‐, Stereo‐ and Regioselective Fluoroallylation/Annulation of Hydrazones with gem‐Difluorocyclopropanes via Tunable Palladium/NHC Catalysis

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(23)

Published: April 4, 2023

Defluorinative manipulation of polyfluorinated molecules has shown great promise due to its granting synthetic versatility inert C-F bonds. The development chemo-, stereo- and regioselective strategies realize highly efficient formation either the linear/branched or E/Z products from gem-difluorocyclopropanes (gem-F2 CPs) is a challenging task. Herein, we have realized palladium/NHC-catalyzed fluoroallylation/annulation hydrazones with gem-F2 CPs that incorporate hydrazone N2 moiety into products. thermodynamically unstable fluorinated E-allylation aryl ketone were obtained for first time, while di-alkyl yielded monofluorinated branched selectivity under similar reaction conditions. With aldehyde hydrazones, two kinds pyrazoles via defluorinative allylation/annulation cascade, in which different carbon atoms could be incorporated pyrazole rings regiospecifically. DFT calculations revealed divergent was kinetically controlled final C-C bond proceeded through 7-membered TS.

Language: Английский

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Recent advances in the synthesis of trifluoromethyl-containing heterocyclic compounds via trifluoromethyl building blocks

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6246 - 6276

Published: Jan. 1, 2024

Recent advances in the preparation of trifluoromethyl-containing heterocyclics via trifluoromethyl building block strategies over period from 2019 to present are systematically summarized and discussed.

Language: Английский

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Recent advances in the synthesis of anticancer pyrazole derivatives using microwave, ultrasound, and mechanochemical techniques

RSC Advances, Journal Year: 2025, Volume and Issue: 15(9), P. 7018 - 7038

Published: Jan. 1, 2025

Pyrazole and its derivatives have attracted considerable attention in pharmaceutical medicinal chemistry, as reflected their presence numerous FDA-approved drugs clinical candidates. This review presents a comprehensive analysis of articles published between 2014 2024, focusing on the microwave-, ultrasound-, mechanochemical-assisted synthesis pyrazole with anticancer activity. It explores synthetic methodologies, efficacy, molecular docking studies, underscoring significance drug discovery chemistry. Notably, microwave irradiation stands out most widely employed technique, providing high efficiency by significantly reducing reaction times while maintaining moderate temperatures. Ultrasound serves valuable alternative, particularly for processes that require milder conditions, whereas mechanochemical activation, though less frequently employed, offers distinct advantages terms sustainability.

Language: Английский

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Electro-oxidative C–H azolation of quinoxalin-2(1H)-ones

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(9), P. 3246 - 3249

Published: Jan. 1, 2021

A practical, general protocol has been developed for direct C–H azolation reactions of quinoxalin-2(1H)-ones by electro-oxidative cross-coupling.

Language: Английский

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