Study On The Sulfonylation Of Alkenes And Alkynes Under Visible Light

Sulfone compounds are widely used in medicine,pesticides,materials science,and organic synthesis.With the development of metal catalysis and photocatalysis,various synthesis strategies have been used to introduce sulfone into organic synthesis.This paper focuses on the sulfonylation of alkenes and alkynes in organic and aqueous phases,and studies the reaction of sulfonyl chloride as a sulfone source.The specific work is as follows:First,the reaction of sulfonyl chloride and alkenes in the organic acetonitrile phase was studied.Although the separated product was a mixture containing the sulfone products ofβ-halosulfone product and vinyl sulfone,the pure vinyl sulfone products could be obtained by treating the mixture in acetonitrile with DBU for 30 minutes at room temperature.Pure vinyl sulfone products can be obtained directly from the two substrates of p-methoxystyrene or p-nitrobenzene sulfonyl chloride.Alkyl sulfonyl chloride such as ethyl sulfonyl chloride and butyl sulfonyl chloride can also directly react to obtain pure vinyl sulfone products.Secondly,the reaction between sulfonyl chloride and alkenes or alkynes in water phase was studied,which could not be reacted directly in pure water,so the surfactant CTAB was added,which could form micelles and other structures in water to promote the reaction.The products of β-iodosulfone and β-iodovinylsulfone were obtained at medium to high yield.It is important to note that the product of the reaction to the methoxystyrene substrate is the same as the vinyl sulfone in the organic phase.Allyl sulfone is the product of n-methyl styrene substrate reaction.Some alkyl alkenes are also suitable for this method.At the same time,alkyl sulfonyl chloride does not react with alkenes in the aqueous phase,which is different from the organic phase.This method is characterized by high efficiency,mild conditions,no transition metal catalyst,water as the solvent,green environmental protection,and good substrate compatibility,which provides a green and efficient synthesis strategy for the introduction of sulfone.