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Relevant academic research and scientific papers

Transition-metal-free C-H oxidative activation: Persulfate-promoted selective benzylic mono- and difluorination

An operationally simple and selective method for the direct conversion of benzylic C-H to C-F to obtain mono- and difluoromethylated arenes using Selectfluor as a fluorine source is developed. Persulfate can be used to selectively activate benzylic hydrogen atoms toward C-F bond formation without the aid of transition metal catalysts.

Cis-specific hydrofluorination of alkenylarenes under palladium catalysis through an ionic pathway

This paper describes the hydrofluorination of alkenes through sequential H- and F+ addition under palladium catalysis. The reaction is cis specific, thus providing access to benzylic fluorides. The mechanism of this reaction involves an ionic pathway and is distinct from known hydrofluorinations involving radical intermediates. The first catalytic enantioselective hydrofluorination is also disclosed. See attached PdF: A series of benzylic fluorides was prepared by hydrofluorination which proceeds through a PdII/IV catalytic manifold. The method is mechanistically distinct from previously reported radical hydrofluorination, and is characterized by its clean regioselectivity and unique cis stereospecificity. The first example of enantioselective net HF addition onto 2-vinylnaphthalene is also disclosed.

An easy access to fluoroalkanes by deoxygenative hydrofluorination of carbonyl compounds via their tosylhydrazones

An efficient and operationally simple synthesis of fluoroalkanes by deoxygenative hydrofluorination of carbonyl compounds via their tosylhydrazone surrogates is reported. The reaction can be carried out in a one-pot procedure directly from carbonyl compounds.

Ionic liquids as recyclable solvents for diethylaminosulfur trifluoride (DAST) mediated fluorination of alcohols and carbonyl compounds

The first simple and efficient method for the synthesis of mono and gem-difluorinated molecules using [C8mim][PF6] ionic liquid as a recyclable solvent medium with diethylaminosulfur trifluoride (DAST) as the fluorinating reagent, is reported.

Cocatalysis in phase-transfer catalyzed fluorination of alkyl halides and sulfonates

Phase-transfer catalyzed (PTC) fluorination of alkyl halides and sulfonates with solid KF proceeds efficiently when cocatalyst triphenyltin fluoride is used. The cocatalytic action of the tin compound consists in continuous formation of difluorotriphenylstannate anion that as the tetraalkyloammonium salt enter the solution where it reacts with alkyl halides to produce alkyl fluorides. The cocatalytic system was used to synthesis of 1,1-difluoroalkanes in two steps from aldehydes. A new kind of PTC was elaborated in which Ph 3SnF acts as phase transfer catalyst via continuous formation of potassium salts of diflurotriphenylstannate anions soluble in dipolar aprotic solvents. A new, simple and general method of synthesis of tetraalkylammonium and potassium salts of difluorotriorgano-tin, silicon and germanium anions is reported.

A new type of phase-transfer catalysis via continuous transfer of fluoride anions to the organic phase in the form of potassium difluorotriphenylstannate

Fluorination of alkyl halides and sulfonates is efficiently executed in a liquid-solid phase-transfer catalysis system with Ph3SnF as phase-transfer catalyst acting via continuous formation of lipophilic Ph 3SnF2 anions entering the organic phase in the form of the potassium salt.

Cocatalysis by tetravalent tin compounds in phase-transfer catalyzed fluorination of alkyl halides and sulfonates

Phase-transfer catalyzed fluorination of alkyl halides or sulfonates is co-catalyzed efficiently by triorganotin halides. The cocatalytic action is due to continuous formation of lipophilic hypervalent triorganodifluorostannate anions, which act as fluori

Selective electrolytic fluorinations in 70% HF/30% pyridine

The selective fluorination of compounds containing benzylic hydrogen atoms was accomplished by electrolysis in a mixture of 70% HF and 30% pyridine (Olah's reagent) using a square wave alternating current (1.76-2.75 V, 0.02-0.05 Hz) and Pt electrodes. This method can be used in the laboratory to prepare conveniently gram-size quantities of monofluorinated products. An ion radical mechanism has been proposed.