Preparation of tri- and difluoromethylsilanes via an unusual magnesium metal-mediated reductive tri- and difluoromethylation of chlorosilanes using tri- and difluoromethyl sulfides, sulfoxides, and sulfones.

doi:10.1021/JO030110Z

Paper

Preparation of tri- and difluoromethylsilanes via an unusual magnesium metal-mediated reductive tri- and difluoromethylation of chlorosilanes using tri- and difluoromethyl sulfides, sulfoxides, and sulfones.

Published May 8, 2003 · G. Prakash, Jinbo Hu, G. Olah

The Journal of organic chemistry

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124

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Abstract

A new and efficient method for the preparation of tri- and difluoromethylsilanes using magnesium metal-mediated reductive tri- and difluoromethylation of chlorosilanes is reported using tri- and difluoromethyl sulfides, sulfoxides, and sulfones. The byproduct of the process is diphenyl disulfide. Since phenyl trifluoromethyl sulfone, sulfoxide, and sulfide are readily prepared from trifluoromethane (CF(3)H) and diphenyl disulfide, the method can be considered to be catalytic in diphenyl disulfide for the preparation of (trifluoromethyl)trimethylsilane (TMS-CF(3)) from non-ozone-depleting trifluoromethane.

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Study Snapshot

This efficient method efficiently prepares tri- and difluoromethylsilanes using magnesium metal-mediated reductive tri- and difluoromethylation of chlorosilanes, yielding diphenyl disulfide as a byproduct.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Preparation of tri- and difluoromethylsilanes via an unusual magnesium metal-mediated reductive tri- and difluoromethylation of chlorosilanes using tri- and difluoromethyl sulfides, sulfoxides, and sulfones.

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References

Citations

Interaction of Difluorocarbene with the Thiocyanate Anion: Access to a Silicon Reagent Bearing the Isothiocyanate Group.

Difluorocarbene interacts with the nitrogen atom of thiocyanate anion, resulting in a silicon reagent bearing the isothiocyanate group, which can be used to create 2-(difluoromethylthio)-4-fluoroimidazoles.

Recent Advances in Fluoroalkylation Strategies: Exploring Novel Reactivities and Synthetic Applications of Sulfone- and Sulfinate-Based Reagents for Mono-, Di-, and Trifluoromethylations

Sulfone- and sulfinate-based reagents offer versatile tools for precise molecular modifications through diverse mechanistic paths, offering diverse routes for controlled molecular modifications.

Developments in the synthesis of allylsilanes by transition metal–catalyzed silylation of 1,3-dienes with disilanes

Transition metal-catalyzed silylation of 1,3-dienes with disilanes enables efficient synthesis of desired allylsilanes in a single step, streamlining silyl-functionalization of 1,3-dienes.

Sulfur-based organofluorine reagents for selective fluorination, fluoroalkylation, and fluoroolefination reactions

Sulfur-based organofluorine reagents enable diverse fluorination, fluoroalkylation, and fluoroolefination reactions, with reactivity tunable by substituents and fluorine atoms.

Synthesis of Azidodifluoromethyl Phenyl Sulfone and Its Use as a Synthetic Equivalent of the Azidodifluoromethyl Anion

Azidodifluoromethyl phenyl sulfone is a stable fluorinated azide that serves as a synthetic equivalent of the azidodifluoromethyl anion, making it useful in the preparation of N-difluoro(phenylsul