Study On The Reaction Of CF₃SO₂Na As Trifluoromethanesulfonylation Reagent

Sodium trifluoromethanesulfinate is a cheap and readily available fluorine-containing reagent,Since Langlois first reported its use in the synthesis of fluorine-containing compounds in 1991,it has a research history of over 20 years.In this paper,in view of the importance of trifluoromethanesulfonyl compounds and the urgent need for efficient trifluoromethanesulfonation methodologies,based on the development of economical and practical trifluoromethanesulfonation methods,we systematically studied on related reactions of CF₃SO₂ Na as a trifluoromethanesulfonylation reagent to achieve trifluoromethanesulfonylation of p-benzoquinone and 4,4-bismethoxycyclohexadien-1-one,respectively.This paper includes two parts.Part one : Trifluoromethanesulfonylation of p-benzoquinones.The cheap and easily available sodium trifluoromethanesulfinate was used as the trifluoromethanesulfonation reagent to study its reaction with p-benzoquinone compounds under iodine additives.Under the promotion of iodine,the reaction of p-benzoquinone with sodium trifluoromethanesulfinate took place to give the corresponding trifluoromethanesulfonylated product in moderate to good yield.Moreover,The reaction of 1,4-benzoquinone imine under the same conditions has also successfully achieved the trifluoromethylsulfonylation of 1,4 benzoquinone imine,and extended to perfluoroalkylsulfonylation.Part two:Trifluoromethanesulfonation of 4,4-bismethoxycyclohexadien-1-one.In the Rf SO₂Na/I₂ system,acetic acid was used as an additive to study the reaction of4,4-bismethoxycyclohexadien-1-one.At room temperature,the4,4-bismethoxycyclohexadien-1-one perfluoroalkylsulfonylation reaction was successfully achieved to give the corresponding perfluoroalkylsulfonylation products in moderate to good yields.The reaction is simple,without the need for transition metals.It is also suitable for the trifluoromethanesulfonylation andperfluoroalkylsulfonylation reactionof 4,4-bismethoxycyclohexadiene-imine?...