Demethylaromatization Of Cyclohexadienones By Iodotriphenylphosphonium Iodide

Structurally complex phenol derivatives are a class of important organic compounds,and have been widely employed as drugs,antioxidants,and ligands,etc.In one issued patent CN107602650,a new method for the one-step conversion of1,4-androstadiene-3,17-dione into estrone mediated by iodotriphenylphosphonium iodide has been reported.In order to broaden the application value of this new method in organic synthesis,in this master’s thesis we carried out the study on the demethylaromatization of cyclohexadienones by iodotriphenylphosphonium iodide.Various steroidal and non-steroidal cyclohexadienone substrates were investigated,and the corresponding phenolic products were smoothly formed in 60-83% yields.This method possesses good functional group tolerance.Additionally,we proposed an ionic synergistic action mechanism to interpret the experimental phenomena.In conclusion,we developed a new method for the demethylaromatization of cyclohexadienones,and provided a new route to prepare multi-substituted phenols.