Application Of Aryl Sulfinic Acid (Sodium) As Sulfone Reagent In The Functionalization Of Alkenes And Alkynes

The sulfone is a key organic structural motif in a variety of biologically active compounds,pharmaceuticals and synthetic intermediates,especially for aryl alkyl sulfones.For example,diaryl sulfones can be used as antiproliferative activity against cancer cell..Therefore,extensive attentions have been paid to the preparation of organic sulfones.Arylsulfinic acids(salts)are relatively stable and versatile intermediates in organic synthesis.In the past decades,considerable efforts have been devoted to the synthesis of organic sulfones using arylsulfinic acids(salts)as sulfonylation reagents.However,the use of toxic and expensive transition metals limits their applicability.Based on the above research background,this article mainly employed light to induce aryl sulfinic acids to generate sulfone radicals,which realized the functionalization of alkenes and alkynes.The contents are as follows:(1)A novel and efficient photo-induced synthesis of C6-polyfunctionalized phenanthridines from three-component reactions of isocyanides,alkynes and sulfinic acids was developed.The reaction was driven by the photochemical activity of novel electron donor-acceptor(EDA)complex,generated from the reaction of arylsulfinic acid and biaryl isocyanide in the presence of pyridine and water.The reactions generated the corresponding products with high selectivity through the photochemical activity of the formed electron donor-acceptor(EDA)complex during the reaction via a radical tandem process under mild conditions.This approach is operationally simple,mild conditions,a broad substrate scope and good yields of the desired products.(2)We describe a novel,efficient,and atom-economic approach which combine selective cross-dehydrogenative coupling of N-arylacrylamides with arylsulfinic acids and direct hydrogenation of C6-(vinyl sulfone)phenanthridines in one-pot under photocatalyst,external oxidant and reductant-free condition,affording an important sulfonated oxindole and hydrogenated product in good to excellent yields.It is should be noted that photo-induced direct O-H band homolytic cleavage of arylsulfinic acids and application of arylsulfinic acids as organic hydrogen donors in hydrogenation of double-double bonds have not been realized.