Sulfur Mediated Allylic C-H Arylation,Epoxidation And Aziridination

The direct allylic C-H bonds functionalization is a hot research topic in synthetic chemistry.Activated sulfoxide intermediates have been widely used in organic synthesis due to their high electrophilicity.We have developed a novel transition metal-free method in which sulfur mediated allylic arylation,epoxidation,and aziridination of olefins through one-pot procedure.The reaction design involves the reaction of diaryl sulfoxide and trifluoromethanesulfonic anhydride to obtain a super-electrophilic sulfonium,which is subsequently eliminated by electrophilic addition reaction with an electron-rich olefin to form an allylic sulfonium intermediate.The sulfonium intermediate is then converted to sulfur ylide by deprotonation of base.Based research on the reaction of activated sulfoxide and olefin,we have verified proposed reaction ideas and explored the application range of semi-stable type allylic sulfur ylide with aryl boronic acids,aldehydes and imines.Sulfur mediated allylic C-H arylation,epoxidation and aziridination reaction have been achieved.