Aziridination And Amidation Reaction Catalyzed By Polymer-supported Metalloporphyrins

Catalytic aziridination and amidation reactions are two important reactions in organic synthesis. Recently, the aziridination/amidation catalyzed by metalloporphyrins attracts considerable interests. This kind of catalysts not only render the reactions undergo gentle condition, but also get high conversions and yields. However, the preparation of metalloporphyrins is difficult, they are unstable and can not be reusable,all these reasons limit their utility. Moreover, most of these reactions are limited in simple hydrocarbons while the macromolecular natural product as substrates has been less reported. In this paper, two easy prepared polymer-supported metalloporphyrins with simple ligands are prepared: MPR Manganese and MPR Ruthenium porphyrins. We use them catalyzed the aziridination of simple olefins and the amidation of saturated CH bonds with "PhI(OAc)2 /TsNH2"in one pot. Both catalysts exhibit high catalytic efficiency. As a result, about 30 percent conversions and moderate yields are got. In the diasteroselective amidation of ?5-steroids derivatives, the polymer-supported Manganese porphyrin exhibits βselective, while the polymer-supported Ruthenium porphyrin is αselective. At the same time, we also investigated the stability and reusability of the catalysts. The results showed the catalysts were stable after consecutively reused four to five times without detectable decline in catalytic efficiency,so the reuse and recycle of the catalysts is realized.