Fluoroalkylation of aromatic compounds with per(poly)fluoroalkyl chlorides initiated by sodium dithionite in DMSO

An Efficient Method for the Preparation of Pentafluoroiodoethane from Chloropentafluoroethane

“…17, 18 Chen 23,24 found that solvent played a pivotal role in this reaction. Using dimethyl sulfoxide (DMSO) as a solvent instead of CH 3 CN/H 2 O (in Na 2 S 2 O 4 /NaHCO 3 ), fluoroalkyl chlorides, even nonfluorinated chlorides such as chloroform can either be converted to the corresponding sulfinate salts or alkylate alkenes and alkynes.…”

Sodium dithionite initiated fluoroalkylation of trimethoxybenzenes, mesitylene and pyrroles with BrCF2CF2Br

“…When more drastic reaction conditions were applied, i.e. water-free dimethylsulphoxide, temperature of 75 8C and prolonged reaction time, perfluoroalkylation of N, S and O heteroaromatics and activated benzenes with long chain perfluoroalkyl chlorides has also been reported [8]. In our laboratory, it has been found that the Na 2 S 2 O 4 /acetonitrile/H 2 O system is also able to promote addition of polyhaloalkanes, i.e.1-bromo-1-chloro-2,2,2-trifluoroethane (Halothane 1 ) [9][10][11][12] and dibromodifluoromethane [13,14] to various electron-rich unsaturated compounds but most attempts to alkylate aromatic and heteroaromatic compounds with these reagents were unsuccessful.…”

“…On this basis, and considering the reported fact that even perfluoroalkyl chlorides are able to Calkylate activated aromatics [8], we undertake studies on the reactions of polymethoxybenzenes, mesitylene and pyrroles with 1,2-dibromotetrafluoroethane, which hopefully should lead to Calkylated product (2-bro-motetrafluoroethyl) aromatics.…”

Chain-radical fluoroalkylation of thiophenols with freon ClCF2CFCl2 in the presence of sulfur dioxide

“…The use of fluorohalocarbons as perfluoroalkyl group synthons for the synthesis of fluorine containing compounds attracted considerable interest [1][2][3][4][5][6][7]. Unlike iodine-and bromine-containing fluoroalkanes, chlorofluoroalkanes (CFCs) as the alkylating agents were explored to a much lesser extent, which is largely caused by their considerably lower reactivity due to stronger C-Cl bond compared to C-Br and C-I.…”