| Oxygenated compounds are widely found in nature such as natural products,various biomass raw materials,etc.Therefore,it is of great significance to realize the functional group conversion of oxygenated compounds by using C-O bond activation to prepare high value-added chemicals.Among them,C(sp~2)-O bond activation with aryl ethers has become a hot research topic in recent years.However,the conversion of aryl ethers faces two main challenges due to the inert C(sp~2)-O bond of aryl ethers.First,the bond dissociation energy of the C(sp~2)-O bond of aryl ethers is relatively high,and the cleavage of such inert C(sp~2)-O bond is thermodynamically difficult.Second,selective activation of one of several oxygenated groups in a complex molecule is challenging.Therefore it is of great importance to explore new methods for C(sp~2)-O bond activation of aryl ethers.Modern organic electrochemistry enables the synthetic transformation of organic compounds in a efficient and“green”way.However,limitations inherent in the established design of experiments in electrochemistry,such as mass and heat transfer and the non-uniformity of the electric field,may sometimes limit the effectiveness of the method.The development of new unconventional methods for conducting electrochemical experiments by making significant modifications to conventional experimental designs may help to overcome these problems.With the development of organic electrochemistry,the use of alternating current for electrochemical synthesis may enable reactions that can’t be efficiently transformed by direct current.The main work of this paper includes the following two parts:1.C(sp~2)-O bond activation by alternating current strategy to construct aryl nitrile compounds:p-aminoanisole with Cbz as the protective group as substrates exchange reactions with functional groups with trimethylsilyl cyanide to obtain the target product with excellent yield.The conditions are mild,the substrate adapts to a wide range,and the target product can be obtained with excellent yields in gram-level reactions.2.C(sp~2)-O bond activation by alternating current strategy,benzoquinone monoketones were constructed.p-methoxyphenol derivatives were used as substrate to reach with alcohol compounds,and benzoquinone monoketones were obtained with relatively high yields.The by-product of the reaction is methanol,which is used without equivalent oxidant,which met the requirements of green synthesis. |
