Application Of Arylsulfinic Acid As Sulfoxidation Reagent In Organic Synthesis

Sulfoxides,as important organosulfur compound,play a significant role in organic chemistry.They serve as versatile bulding blocks in organic synthesis and are extensively used in pharamaceutical,plastics and industry of fine chemicals.Furthermore,chiral sulfoxides as chiral auxiliaries and ligands have been used in asymmetric synthesis.Therefore,great interest from chemists have been paid to the preparation of sulfoxides.However,the direct synthesis of sulfoxides remains a challenge.Besides the selective oxidation of sulfides,the nucleophilic substitution of sulfinyl derivatives with organometallic represents the significant method for the preparation of sulfoxides.However,harsh reaction conditions or multistep strategies limited the application of these methods in organic synthesis.Thus,the development of direct and efficient approach for selectively preparing diverse sulfur-containing compounds is highly desired.In this paper,we disclosed an efficient methodology for the preparation of diaryl sulfoxides,m-arylthio sulfones,and β-sulfonylvinyl sulfoxides by employing readily available arylsulfinic acid as staring material.The contents are as follows:(1)We have developed a novel and effective approach for selectively preparing diverse diaryl sulfoxides and m-arylthio sulfones from arylsulfinic acids and arenes via an unusual sulfinyl cation.The method proceeds under mild reaction conditions and produces a wide range of diaryl sulfoxides and m-arylthio sulfones in good yields with good functional group tolerance.(2)A nolve and efficient difunctionalization of alkynes was developed for the synthesis of β-sulfonylvinyl sulfoxides with high region-and stereoselectivity from commercially available arylsulfinic acids and alkynes.This protocol provides a direct access to β-sulfonylvinyl sulfoxides with good functional groups tolerance in absence of metal catalyst and additive under mild condition.