Silver Catalyzed Coupling Reaction Of Styrene With Sodium Benzenesulfonate

Vinyl sulfone compounds,skeleton of many drugs and significant drug intermediates,is widely applied in the area of chemistry,medicine and pesticide.In addition,sulfone functional groups is easily attached and removed under the mild condition and vinyl sulfone becomes the intermediates of many new dyes and fine chemicals.Due to the wide application value of vinyl sulfone compounds,efficient synthesis methods have raised widely attention,many of which reported by scientists are high efficient and convenient.On the basis of extensive investigation,a new method,coupling reaction of silver-catalyzed styrene and sodium benzene sulfite,is proposed and the possible mechanism is suggested in this paper.The main work and conclusions are as follows:1.Vinyl sulfone compounds are synthesised by coupling reaction of silver-catalyzed styrene and sodium benzene sulfite and the yield rate is 82%.The possible mechanism is as follows:after flitering the following essentials:the reaction catalyst,oxidant,additive,solvent and temperature,the optimum reaction condition is:0.2 mmol styrene,0.2 mmol benzenesulfinate,0.03 mmol silver nitrate,0.4 mmol potassium persulfate,0.04 mmol TEMPO,1 mL toluene,reaction for 10 hours at 100 ^oC.2.Under the optimum synthetic conditions,the coupling reaction is successful with different replacements of substrates.And the target product,vinyl sulfone compounds is yielded.Including:?1?The outcome showing the yield rate is 61%-88%,if we replace the substrates of styrene with styrene including electron-attracting,such as F,Cl,Br,NO₂ and etc,and electron-donating group such as CH₃,CH₃O etc.?2?The outcome showing the yield rate is 70%,if we replace the substrates of styrene with heterocyclic compounds2-vinylthiophene,the yield rate is 81%-84%,and if we replace the substrates of styrene with cyclic olefins 1,2-dihydronaphthalene and indene.?3?The outcome showing:we use sodium benzenesulfinate with different substituent group,including electron-attracting,such as F,Cl,Br and etc,and electron-donating group such as NO₂,CH₃,CH₃O and etc,reaction with the styrene with different substrates smoothly and the yield rate is 60%-86%.