Study On The Construction Of C-C And C-N Bonds Based On C-H Activation Of Electron-Deficient Aromatic Hydrocarbons Participated By T-BuONa

Electron-deficient?hetero?arene derivatives play an important role in various drugs,natural products and synthetic new materials.Nitroaromatic compounds are important as electron-deficient derivatives in organic synthesis and pharmaceutical synthesis.Nitroaromatic compounds are commonly used to construct various chemical bonds such as C-N,C-C,and C-X.However,the conventional construction methods have the disadvantages of high temperature,metal catalysis,low conversion rate,and high cost.Therefore,the synthetic methods of electron-deficient?hetero?aromatic hydrocarbon derivatives with high efficiency,economy and environmental benign are increasingly concerned by chemists.In this paper,some work has been carried out on the synthesis of electron-deficient?hetero?arene derivatives.We achieved monosubstituted nitration and disubstituted nitration of4-phenyltetrahydroquinoline derivatives without the addition of a metal catalyst.4-Phenyltetrahydroquinoline derivative was obtained in DMSO solvent with metal-free catalyst,t-BuONa as base,4-phenyltetrahydroquinoline derivative and nitrobenzene as substrate in O₂ atmosphere.Construction of C-N and C-C bonds with nitrobenzene.In this embodiment,the distribution ratio of the two nitration products is selectively changed by the difference in according with the amount of the base and the nitrobenzene added.Inspired by this,we mainly synthesize a substituted nitrated product.The reaction system not only realizes the construction of C-N bond and C-C bond in the absence of metal catalyst,but also can change the distribution ratio of the two nitrated products.The reaction substrate has good tolerable and excellent yields,and conforms to the purpose of green chemistry.We changed the type of electron-deficient?hetero?aromatics to achieve a one-substituted nitration of 4-phenyltetrahydroquinoline derivatives.Under the absence of a metal catalyst,t-BuONa was used as a base,and 4-phenyl was used in an O₂ atmosphere.The tetrahydroquinoline derivative and the nitronaphthalene are substrates,and the C-N bond structure of the 4-phenyltetrahydroquinoline derivative and the nitronaphthalene is realized in a DMSO solvent.The reaction avoids the utilization of a metal catalyst,and the reaction suitability is good,and the target product can be obtained in a good yield.