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Issue 12, 2012
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Progress in fluoroalkylation of organic compounds via sulfinatodehalogenation initiation system

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Abstract

The sulfinatodehalogenation reaction represents one of the most important methodologies to incorporate fluorine into organic molecules. Using inexpensive sulfur-containing reactants such as Na2S2O4 under mild conditions, per- and polyfluoroalkyl halides (RFX, X = Br, I, CCl3) can be transformed smoothly into the corresponding sulfinate salts. This method is also used for the perfluoroalkylation of alkenes, dienes, alkynes and aromatics. Notably, after 1998, the sulfinatodehalogenation of perfluoroalkyl chlorides (RFCl) has been realized by using dimethylsulfoxide (DMSO) as a solvent instead of CH3CN/H2O in the Na2S2O4/NaHCO3 initiation system. Perfluoroalkyl chlorides, ethyl chlorofluoroacetates and chlorodifluoroacetates, and even nonfluorinated compounds, such as ethyl chloro- or dichloroacetates and chloroform, were either converted into the corresponding sulfinate salts or alkylated alkenes, alkynes and aromatics (including porphyrins). The sulfinatodehalogenation reaction has remarkable advantages. With the increasing demands to utilize the unique properties of fluorine and fluorinated functional groups in medicinal, agricultural and material sciences, we believe that there will continue to be useful developments in sulfinatodehalogenation chemistry and it will be applied more widely in the future.

Graphical abstract: Progress in fluoroalkylation of organic compounds via sulfinatodehalogenation initiation system

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Publication details

The article was received on 22 Dec 2011 and first published on 17 Apr 2012


Article type: Critical Review
DOI: 10.1039/C2CS15352A
Citation: Chem. Soc. Rev., 2012,41, 4536-4559
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    Progress in fluoroalkylation of organic compounds via sulfinatodehalogenation initiation system

    C. Zhang, Q. Chen, Y. Guo, J. Xiao and Y. Gu, Chem. Soc. Rev., 2012, 41, 4536
    DOI: 10.1039/C2CS15352A

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