Sodium Trifluoromethanesulfinate

Ye, Yingda

doi:10.1002/047084289x.rn01689

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Encyclopedia of Reagents for Organic Synthesis 2014

DOI: 10.1002/047084289x.rn01689

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Sodium Trifluoromethanesulfinate

Yingda Ye

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Cited by 2 publications

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Recent Advances on the Application of Langlois’ Reagent in Organic Transformations

et al. 2021

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Langlois’ reagent (trifluoromethanesulfinate salt) has been proven to be a valuable reagent for the synthesis of various classes of molecules, mainly trifluoromethylated compounds, in academic, biological and industrial research. Synthetic uses of Langlois’ reagent in organic transformations of aromatic and heteroaromatic compounds, alkenes, alkynes, boronic acids, carboxylic acids, and etc are discussed.This review aims to demonstrate the ongoing utility of Langlois’ reagent in the preparation of various classes of organic compounds. Furthermore, to address the recent collective papers, the current review summarizes and comprehensively describes manuscripts on synthetic applications of Langlois’ reagent since 2015 until today.

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Recent Advances on the Application of Langlois’ Reagent in Organic Transformations

et al. 2021

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Two-step conversion of carboxylic esters into distally fluorinated ketones via ring cleavage of cyclopropanol intermediates: application of sulfinate salts as fluoroalkylating reagents

et al. 2017

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Tertiary cyclopropanols easily available from carboxylic esters have been used in the synthesis of distally fluorinated ketones. Cyclopropane ring cleavage reactions in methanol with aqueous tert-butyl hydroperoxide in the presence of a copper(ii) acetate catalyst and sodium triflinate (Langlois reagent) afford β-trifluoromethyl ketones in 16-74% isolated yields. Sodium triflinate serves as a precursor of reactive trifluoromethyl copper species, enabling ring-opening trifluoromethylation, as evidenced by mechanistic studies. We also demonstrate here that other sulfinate salts, such as sodium 1,1-difluoroethanesulfinate, sodium 2-(4-bromophenyl)-1,1-difluoroethanesulfinate and sodium 1-(trifluoromethyl)cyclopropanesulfinate, can be used as fluoroalkylation reagents, resulting in the corresponding fluorinated ketones.

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Sodium Trifluoromethanesulfinate

Cited by 2 publications

References 24 publications

Recent Advances on the Application of Langlois’ Reagent in Organic Transformations

Recent Advances on the Application of Langlois’ Reagent in Organic Transformations

Two-step conversion of carboxylic esters into distally fluorinated ketones via ring cleavage of cyclopropanol intermediates: application of sulfinate salts as fluoroalkylating reagents

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