Perfluoroarylation Reaction Of Thiophenol/Phenol And Synthesis Of Pentafluorophenyl Hypervalent Iodine Reagent

Organic fluorine compounds are widely used in social life and production and have special application value.The fluorine atom is a very special element.The introduction of fluorine atoms or fluorine-containing groups into compounds can significantly change the physical and chemical properties of these substances.Therefore,it is of great research value and significance to find an excellent method to introduce fluorine-containing atoms or groups into organic compounds.High-valent iodine reagents have the advantages of low toxicity,environmental friendliness,cheap and easy availability,and are used as oxidants or transfer reagents in many reactions.Since high-valent iodine reagents containing fluorine sources have been continuously discovered,we can synthesize more different organic fluorides.This article studies the reaction of nonafluorobiphenyl hypervalent iodine reagent with phenol/thiophenol,and explores a synthetic method of pentafluorobenzene hypervalent iodine reagent.The main contents are as follows:1)In this paper,a method for the synthesis of nonafluorobiphenyl phenyl sulfide and derivatives using nonafluorobiphenyl hypervalent iodine reagent（0.10 mmol,1.0 equiv.）and thiophenol and its derivatives（2.0 equiv.）as substrates has been developed.good idea.The author of this article has conducted an in-depth investigation of the reaction conditions and determined that under argon and room temperature,cuprous thiocyanate（25 mol%）and 1,10-phen（25 mol%）are used as the catalyst and ligand,respectively.K₂CO₃（2.0 equiv.）is used as the base,and the optimal conditions for the reaction for 12h in 2 ml of DCM solvent.Various nonafluorobiphenyl phenyl sulfide compounds synthesized with a yield of 29%-81%.A possible mechanism for the reaction is proposed.2)This article has developed a good method to synthesize nonafluorobiphenyl ethers and derivatives using nonafluorobiphenyl hypervalent iodine reagent（1.0 equiv.）and phenol（1.5 equiv.）and derivatives as substrates.The author of this article has conducted an in-depth study of the reaction conditions and determined that Pd（amphos）Cl₂（5 mol%）is used as a catalyst,Ag₂CO₃（1.0 equiv.）is used as an additive,K₃PO₄（2.0 equiv.）is used as a base,and 2 ml of DMF is used as the solvent,and the reaction conditions are optimal for 12 h at 120 ^oC.Various octafluorobiphenyl phenyl ether compounds synthesized with 38%-92%yield.A possible mechanism for the reaction is proposed.3)This article explores the synthesis of Togni II type pentafluorophenyl hypervalent iodine reagent,and designs a variety of synthetic routes.Chloriodane is synthesized by the chlorination reaction of 2-iodobenzoic acid and TCICA,and the reaction is carried out by the silicon reagent method using chloroiodane as a raw material.Starting from2-iodobenzoic acid,it reacts with pentafluorobenzene or bromopentafluorobenzene through potassium sulfate oxidation.