Fluorination and fluoroalkylation of alkenes/alkynes to construct fluoro-containing heterocycles

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(9), P. 2079 - 2109

Published: Jan. 1, 2021

This review summarize the established strategies through fluorination and fluoroalkylation of alkenes/alkynes for constructing fluoro-containing heterocycles. Reaction scopes, mechanisms some shortcomings are also discussed.

Language: Английский

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Cyanation with isocyanides: recent advances and perspectives

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(12), P. 1546 - 1562

Published: Jan. 1, 2024

This review focuses on the cyanation of isocyanides with recent advances and perspectives.

Language: Английский

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Controllable Single and Double Difluoromethylene Insertions into C–Cu Bonds: Copper-Mediated Tetrafluoroethylation and Hexafluoropropylation of Aryl Iodides with TMSCF₂H and TMSCF₂Br

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(27), P. 12202 - 12211

Published: July 5, 2022

The selective difluoromethylene insertion into a C–Cu bond is challenging task and currently limited to either single CF2 CuCF3 or double insertions CuC6F5 (or (Z)-CF3CF = CFCu). Achieving both the same even more difficult. Herein, highly controllable CuCF2H species with TMSCF2Br reagent have been described, affording two previously unknown fluoroalkylcopper "Cu(CF2)nCF2H" (n 1 2) independently under different reaction conditions. This work represents first example of in manner. synthetic value obtained demonstrated by their reactions aryl iodides, halogenation agents, cinnamyl chloride, which enables direct transfer HCF2CF2 HCF2CF2CF2 moieties organic molecules. key fluorocarbon chain elongation from C1 C2 C3 presumably attributed reactivities 0, 1, 2 3) loading reagent.

Language: Английский

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TMSCF₂Br‐Enabled Fluorination–Aminocarbonylation of Aldehydes: Modular Access to α‐Fluoroamides

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 61(8)

Published: Dec. 16, 2021

A protocol for the modular assembly of α-fluoroamide motif has been developed, which provides a practical method efficient synthesis structurally diverse α-fluoroamides from easily available aldehydes and tertiary amines through three-component fluorination-aminocarbonylation process. The key to success this process is taking advantage multiple roles unique difluorocarbene reagent TMSCF2 Br (TMS=trimethylsilyl). mechanism involves 1,2-fluorine oxygen migrations in situ formed TMS-protected α-aminodifluoromethyl carbinol intermediates, represents new type deoxyfluorination reaction.

Language: Английский

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Base-controlled selective cleavage of the C–F bond of difluorocarbene for the divergent assembly of indolizines

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4214 - 4218

Published: Jan. 1, 2024

A [3 + 1 1] cascade annulation reaction for the divergent construction of trisubstituted indolizines using sulfoxonium ylides, BrCF 2 CO Me and pyridinium salts as readily available substrates has been developed.

Language: Английский

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In Situ Generation of Unstable Difluoromethylphosphonate-Containing Diazoalkanes and Their Use in [3 + 2] Cycloaddition Reactions with Vinyl Sulfones

Organic Letters, Journal Year: 2021, Volume and Issue: 23(3), P. 1130 - 1134

Published: Jan. 22, 2021

A [3 + 2] cycloaddition reaction of unstable difluoromethylphosphonate-containing diazoalkanes with vinyl sulfones under simple conditions is developed, which provides an efficient route toward functionalized fluorinated pyrazolines derivatives in good chemical yields. The difluoro are generated situ using t-BuONO for the diazotization (β-amino-α,α-difluoroethyl)phosphonates, and their stabilities reactivities were carefully investigated.

Language: Английский

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Synthesis of polysubstituted pyrrolesviaisocyanide-based multicomponent reactions as an efficient synthesis tool

New Journal of Chemistry, Journal Year: 2021, Volume and Issue: 45(47), P. 21967 - 22011

Published: Jan. 1, 2021

The present review covers all synthetic methods based on isocyanide-based multicomponent reactions for the preparation of polysubstituted pyrroles as parent cores many essential drugs, biologically active compounds, and compounds with wide application in materials science.

Language: Английский

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Ring-fluorination of heterocycles using chemical and electrochemical methods

Advances in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

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Modular Synthesis of Monofluorinated 1,2,4-Triazoles/1,3,5-Triazines via Defluorinative Annulations of N-CF₃ Imidoyl Chlorides

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 10, 2025

Ring-fluorinated azaheterocycles have wide applications in agrochemicals, pharmaceuticals, and synthesis, which prompt continuous endeavors to expand such heterocyclic families. However, monofluorinated triazaheterocycles hardly been explored. This work reported a novel modular synthesis of 1,2,4-triazoles 1,3,5-triazines, utilizes N-CF3 imidoyl chlorides as unique polyfluoro synthons their defluorinative annulations with hydrazines/imidazines. Further modifications these fluorinated heterocycles highlight the potential method for accessing functional molecules.

Language: Английский

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Advances in the Synthetic Utility of Difluorocarbene Generated from TMSCF₃ (Ruppert‐Prakash Reagent) and Its Derivatives

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: March 12, 2025

Abstract Organofluorine compounds are of pivotal significance particularly, in drug and agrochemical industries different strategies have been designed for their synthesis. The last two decades witnessed the emergence difluorocarbene as an efficient synthetic tool, providing easy access to organofluorine compounds. This review summarises reactions generated from Ruppert‐Prakash reagent (TMSCF 3 ) its derivatives TMSCF 2 Cl Br. Among various fluorination techniques available, chemistry offers a cost effective procedure, opening avenue large number details developments utility derivatives, till date.

Language: Английский

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