Application Of Phenyltrifluoromethyliodine In Thiol Trifluoromethylation

Trifluoromethyl-containing compounds have important applications in medicine,pesticides,and organic materials,mainly because the introduction of trifluoromethyl groups can increase the lipophilicity and stability of the compounds.The development and use of different trifluoromethyl sources is an important approach to the development of trifluoromethylation reactions.The hypervalent iodine CF₃ reagents prepared by Togni's group have been rapidly developed in the field of trifluoromethylation in recent years.However,the price is expensive,the synthesis steps are cumbersome,and the reaction generally needs to be activated.Our group carried out the work on the synthesis of acyclic hypervalent iodine CF₃reagents.The cost of the substrates was inexpensive,the operation of the synthesis was simple,and the reagent can be stable in room temperature and normal atmosphere.Recently,we mainly explored the activity and application of this reagent.Based on our work,combined with the previous trifluoromethylation work of thiols,we select the thiols as a soft nucleophile to react with the reagents in this paper.Tests were carried out to achieve direct trifluoromethylation of thiols using our reagents.The main contents are as follows:1.The introduction includes two parts in this paper:?1?Outline the electrophilic trifluoromethylation reaction;?2?The research progress of the trifluoromethylthio-containing compounds was summarized.2.A direct trifluoromethylation reaction of aliphatic thiols,thiophenols and heterocyclic mercaptans with our reagents was realized under the action of NEt₃ in this paper.Seventeen trifluoromethylthio-containing compounds were synthesized and characterized by ¹H NMR?¹⁹F NMR and MS spectrum.This is a new method for synthesizing trifluoromethylthio-containing compound by using an acyclic hypervalent iodine CF₃reagents and thiols.By researching our reagents,we found that the mechanism of the reaction is different from the mechanism of the thiol trifluoromethylation reaction by Togni reagents.In addition,our reagents can be used as a new electrophilic trifluoromethyl source.The reactivity of thiophenols substrates is comparable to Togni's reagents,and the reactivity of secondary aliphatic thiol substrates is better than Togni's reagents.