Polyfluoroalkyl iodides

Aminopyridines can be perfluoroalkylated in a photoinduced electron transfer process. A charge transfer complex between the heterocycle and polyfluoroalkyl iodide, observable by NMR, is photolytically stimulated... 

Perfluoroalkyl iodides RfI and polyfluoroalkyl iodides of the type of RfCH2CH2I are directly oxidizable. Their oxidation potentials are summarized in Table 3 [35],... 

Elimination of hydrogen iodide from polyfluoroalkyl iodides is facile and gives fluoroal-kenes. Hydrogen iodide is easily eliminated by strong bases (e. g., sodium hydroxide) from polyfluoroalkyl iodides to give the fluoroalkenes.8... 

The relative catalytic activities of the Ni group metals in the reactions of perfluoroalkyl and polyfluoroalkyl iodides with amines to give enamines were compared, and the reactivity order Ni > Pd > Pt was found523. 

Pd(PPh3)4-Catalysed reaction of perfluoroalkyl and polyfluoroalkyl iodides, e.g. CF3(CF2)2CF2l and Cl(CF2)5CF2l, respectively, with R2NH (R = Et, Pr, Bu) gave 40-50% of enamines, e.g. CF3(CF2)3CH=CHNR2 and CKCFjieQMel CHNRj, which on hydrolysis with 2 M HCl afforded 95% of enaminones. ... 

Polyfluoroalkylaldehydes. " Polyfluoroalkyl iodides are metalated by treatment of Al powder and catalytic amounts of PbBr2. The in situ reaction with DMF solvent gives the aldehydes. 

Carboxylation of polyfluoroalkyl iodides. Catalyzed by AgNOs, the functionalization of polyfluoroalkyl iodides by transfer of the carboxyl group from HCOONa is a valuable procedure because of its simplicity. 

Polyfluoroalkyl iodides react regioselectively with furan to form 2-polyfluoroalkyl derivatives in the presence of catalytic amounts of tetrakis(triphenylphosphine) nickel at 60-80° C. 

Perfluoroalkyl iodides Rfl and polyfluoroalkyl iodides of RfCH2CH2l type can be directly oxidized (see the oxidation potential data summarized in Table 4). ... 

Commercially Interesting Materials from Polyfluoroalkyl Iodides,—Rp(CHj)2l + EtOH, A NH,OH(aq), A... 

Fluoroalkyl-l -pyrazoles 58 were synthesized in excellent yields in one-pot procedure starting from polyfluoroalkyl iodides 56 [30]. The treatment of 56 wi(h ethylvinyl ether led to their corresponding fluoroalkyl aldehyde intermediates 57, which upon condensation with hydrazine acetic acid under mild conditions gave pyrazoles 58 (Scheme 17). 

Polyfluoroalkyl iodide (1 eq.) is added to a solution of bis(Af,A -bistrimethylsilylamino)-stannane(II) (1 g) in anhydrous THF (10 mL) under an argon atmosphere at room temperature. The reaction mixture is stirred at room temperature until the reaction mixture turned pale yellow. The solution is then concentrated in vacuo to furnish the corresponding Sn(IV) reagent. TBAF (5.9 mL, 3 eq., 1 M in THF) is then added in situ at room temperature. The reaction mixture is concentrated in vacuo before addition of anhydrous dioxane (8 mL), the catalyst (1 mol%) and iodobenzene (1.23 mmol. 0.6 eq.). The reaction mixture is heated at 101 °C for 105 min before cooling to room temperature. Removal of solvent in vacuo yields an oily residue, which is chromatographed on silica gel (petroleum ether) to give the cross-coupled product in 89% yield. ... 

On the other hand, in the case of benzoyl fluoride, the reaction is very slow and does not lead to the ultimate formation of a tertiary alcohol, but of the product 24 of the esterification of benzoic acid by the tertiary alcohol.Benzoyl chlorides react with perfluoroalkyl iodides in the presence of tris(diethylamino)phosphane in a nonpolar solvent to give the corresponding polyfluoroalkyl aryl ketones 25 via substitution of the chlorine. 

Section II.H). The presence of further halogen atoms or other reactive sites in the reactants adds a further complicating feature. Diethyl phosphorochloridate reacts with several polyfluoroalkylmagnesium iodides to give diethyl (polyfluoroalkyl)phosphonates, which include the perfluorohexyl, the co-chloroperfluoroalkyl series C1(CF2) (n = 4,6 or 8) and F02S(CF2)20(CF2)4. ... 

The ratio of 2, 3, and 4 isomers formed in the reaction of pyridine (8) with polyfluoroalkyl bromides and iodides ( 5 5 1) is approximately constant in all theses reactions and is consistent with free radical mechanism of the process. Quinoline and... 

Copper (s, a. under Zn) (Polyfluoroalkyl)arenes from ar. iodides... 

Polyfluoroalkyl phosphonium iodides, RfsRPI (Rf = C4F9C2H4, and CgF] 7C2H4 R=M.e, Rf), cata-... 

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