title: Progress in fluoroalkylation of organic compounds via sulfinatodehalogenation initiation system.
abstract: The sulfinatodehalogenation reaction represents one of the most important methodologies to incorporate fluorine into organic molecules. Using inexpensive sulfur-containing reactants such as Na(2)S(2)O(4) under mild conditions, per- and polyfluoroalkyl halides (R(F)X, X = Br, I, CCl(3)) 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 (R(F)Cl) has been realized by using dimethylsulfoxide (DMSO) as a solvent instead of CH(3)CN/H(2)O in the Na(2)S(2)O(4)/NaHCO(3) 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.
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
authors.forename: Cheng-Pan
authors.initials: CP
authors.lastname: Zhang
authors.forename: Qing-Yun
authors.initials: QY
authors.lastname: Chen
authors.forename: Yong
authors.initials: Y
authors.lastname: Guo
authors.forename: Ji-Chang
authors.initials: JC
authors.lastname: Xiao
authors.forename: Yu-Cheng
authors.initials: YC
authors.lastname: Gu
mesh_terms: D000478:Alkylation; D017611:Fluorine Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D009930:Organic Chemicals / Q000138:chemical synthesis / Q000737:chemistry*; D013457:Sulfur Compounds / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D017611:Fluorine Compounds; D009930:Organic Chemicals; D013457:Sulfur Compounds