Fluorination

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Sulfonyl chlorides are often chosen as building blocks in medicinal chemistry for their ability to easily react with heterocyclic amines to create complex sulfonamides.

Deoxyfluorination with 2-Pyridinesulfonyl Fluoride (PyFluor)

The prevalence of organofluorine compounds in industry and drug design necessitates the ability to introduce C–F bonds to molecules.

Trimethyl(trifluoromethyl)silane (Ruppert–Prakash Reagent)

Technical article for Trimethyl(trifluoromethyl)silane (Ruppert–Prakash Reagent)

Diethylaminosulfur Trifluoride (DAST)

Diethylaminosulfur trifluoride (DAST) is ideal for nucleophilic fluorination and has been used in selective fluorinations of alcohols, alkenols, carbohydrates, ketones, sulfides, epoxides, thioethers, and cyanohydrins.

AlPhos and [(AlPhosPd)₂•COD] for Pd-Catalyzed Fluorination

Fluorine containing aromatics (ArF) are desirable compounds with applications in medicinal chemistry and the agricultural industry.

Fluoroalkylation: Expansion of Togni Reagents

The fluoroalkylation toolbox now includes Togni reagents, hypervalent iodine perfluoroalkylation reagents, fluoroalkyl bromides, silanes, carboxylates, and sulfonyl fluorides for late stage fluoroalkylation.

Fluorinated Azides: Click Chemistry Meets Fluorine

Fluorinated azides are a new tool that can be used to introduce fluorinated groups to molecules. These molecules can utilize click chemistry to easily add fluorinated groups.

Trifluoromethylator™, A Robust Arene Trifluoromethylation Reagent: (Phen)Cu-CF3*

(Phen)Cu-CF3 (cat. #L510009) is an easily handled, thermally stable, single-component reagent for the trifluoromethylation of aryl iodides.

Recent Advances in the Catalytic Transformations

This article details the latest progress in synthesizing alkylsulfonyl fluorides through different approaches that utilize photoredox catalysis, electrocatalysis, transition-metal catalysis, and organocatalysis. The alkylsulfonyl fluorides thus prepared could be utilized further in sulfur(VI) fluoride exchange (SuFEx) click reactions.

TADDOL

The chiral auxiliaries TADDOLs (α,α,α,α-tetraaryl-1,3-dioxolane-4,5- dimethanols) developed by Seebach's group have found numerous applications in asymmetric synthesis ranging from utilization as stoichiometric chiral reagents or in Lewis acid mediated reactions, to roles in catalytic hydrogenation and stereoregular metathesis polymerization.

AISF: A Stable, Solid Alternative to Sulfuryl Fluoride Gas

A solid and bench-stable alternative to sulfuryl fluoride gas has been developed, 4-(Acetylamino)phenyl]imidodisulfuryl difluoride (ASIF). ASIF is a shelf-stable, crystallilne reagent for the installation of the valuable SO2F functional group.

XtalFluor-E^® and XtalFluor-M^®: Convenient, Crystalline Deoxofluorination Reagents

This is an article regarding XtalFluor-E® and XtalFluor-M®: Convenient, Crystalline Deoxofluorination Reagents.

PhenoFluor™ Solution for Convenient, One-step Deoxyfluorination

The functional-group-tolerant, one-step conversion of phenols to aryl fluorides is a highly desirable process. PhenoFluor™ solution, provides straightforward method to fluorinate alcohol and phenols without preactivation and regioselectively fluorinate highly functionalized late-stage intermediates.

Selectfluor™

Selectfluor™ (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), or F-TEDA) is a user-friendly, mild, air- and moisture-stable, non-volatile reagent for electrophilic fluorination.

Acid Halogenation Reagents

Fluoroamidinium salts were an advance in acid halogenation. Compared to chlorides, acid fluorides have greater water stability and a lack of conversion to the corresponding oxazolones upon treatment with organic bases.