Oxidation-induced Radical Oxidative Cross -Coupling Efficient Building C-N/C-S Bond

The development of organic chemical synthesis methodology has laid a foundation for the rapid development of modern society.The synthesis of carbon-hetero bond compounds has attracted much attention from chemists based on their important role in pesticides,medicines,functional materials and other aspects.The development of simple and green synthesis methods for efficient construction of carbon-hetero bond compounds from hydrocarbons and hetero-hydrogen compounds has been a hot topic.In recent years,oxidation induced activation of C-H bond to construct carbon-hetero bond is a very effective synthesis method,which has the advantages of high atomic economy.In this dissertation,Iron-catalyzed coupling of C-H bonds and C-H bond activation amination of aromatic compounds are introduced.Based on the above summary and the oxidization-induced activation strategy,we designed the Iron-catalyzed oxidation-induced free radical cross-coupling reaction to construct C-S bond,and K₂S₂O₈-induced azolation of phenol derivatives to construct C-N bond.The relevant research results are as follows:1.The application of iron-catalyzed C-H bond oxidation coupling reaction in the construction of C-S bond was expanded through literature investigation.Through the reaction system of iron catalyst and TBHP oxidant,we successfully realized the free radical cross-coupling reaction of naphthol compound and phenylsulfinic acid to build C-S bond.2.We have designed a reaction to construct arylazole compounds with an oxidation-induced one-electron transfer strategy.We use K₂S₂O₈ oxidation to induce N-H bonds of azole compounds to generate nitrogen-centered radicals,and then react with phenol derivatives to synthesize a series of arylazole compounds.This method is simple,efficient,and verified by EPR experiments that K₂S₂O₈ oxidation induces N-center free radicals from pyrazole.