96791-89-8Relevant academic research and scientific papers
Radical Perfluoroalkylation Enabled by a Catalytically Generated Halogen Bonding Complex and Visible Light Irradiation
Tasnim, Tarannum,Ryan, Calvin,Christensen, Miranda L.,Fennell, Christopher J.,Pitre, Spencer P.
supporting information, p. 446 - 450 (2022/01/04)
Exploiting charge-transfer complexes in visible light-promoted single-electron redox reactions is a promising route for opening novel synthetic pathways, and catalytic approaches to complex formation are critical for facilitating this chemistry. This report describes the use of a substituted hydroquinone catalyst to promote radical perfluoroalkylation reactions. Mechanistic studies indicate that the reaction is initiated through formation of a visible light-absorbing halogen bonding complex between the hydroquinone catalyst and the perfluoroalkyl halide radical precursor.
Reaction of Perfluoroalkyl Iodides with Electron Donor Nucleophiles. Addition of Perfluoroalkyl Iodides to Olefins Initiated by Electron Transfer
Feiring, Andrew E.
, p. 3269 - 3274 (2007/10/02)
The radical chain addition of primary and secondary perfluoroalkyl iodides to olefins is initiated by sodium arene- and alkanesulfinates.The process occurs at room temperature and is favored by the use of dipolar aprotic solvents.The reaction of perfluorooctyl iodide with sodium p-toluenesulfinate in the absence of olefin requires higher temperatures and gives only 1-H-perfluorooctane; no anion-perfluoroalkyl radical coupling products were detected.Reaction of perfluorooctyl iodide with the sodium salt of diethyl methylmalonate also gives no coupling product; only 1-H-perfluorooctane and a dimer of the malonate anion are produced.These results are compared with the reaction of perfluoroalkyl iodides with nitronate and thiolate anions where formation of SRN1 substitution products was observed.
