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CF0014 Sigma-Aldrich

Phenylsulfanyltetrafluorobromoethane

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Properties

Related Categories Chemical Synthesis, Fluorination Reagents, Perfluoroalkylation, Synthetic Reagents
form   liquid

Description

Application

Phenylsulfanyltetrafluoroethyl bromide is a fluoroalkylbromide that is a radical source of the phenylsulfanyltetrafluoroethyl moiety. Alternatively, it can also be selectively metallated at the fluorinated carbon with Turbo Grignard reagent at low temperatures resulting in a thermally unstable anion that can act as a nucleophilic fluoroalkylation reagent towards a wide variety of electrophiles, such as aldehydes, ketones or sulfonylimines. A phenylsulfanyltetrafluoroethyl moiety incorporated in the substrate can be treated with tributyltin hydride and generate the corresponding fluoroalkyl radical. If the substrate lacks any olefins, it can be reduced to tetrafluoroethyl group whereas if the substrate contains an olefin in a correct spatial orientation, it can lead to an intramolecular cyclization affording tetrafluorinated cyclic structures.

Other Notes

Technology Spotlight: Fluoroalkylation: Expansion of Togni Reagents

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Protocols & Articles

Articles

Fluoroalkylation: Expansion of Togni Reagents

The installation of highly fluorinated groups into drug and pesticide candidates is a powerful strategy to modulate their properties. An incorporated fluorinated sidechain can tune the acidobasic beh...
Keywords: Catalysis, Chlorinations, Cyclizations, Degradations, Fluorinations, Grignard Reaction, Pesticides, Radical cyclization

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