Study On The C₅-H Bromination Of 8-aminoquinoline Induced By Visible Light Or Electric Reduction

Organic halogenated compounds,as synthetic intermediates,are widely used in chemical industry,medicine,agricultural products and other important raw materials.In recent years,aryl direct C-H functionalization research has developed from transition metal catalysis to metal-free catalysis,even now photochemistry or electrochemistry,which has injected new power and blood into the continuous development of C-H functionalization.Visible and electrochemistry are now favored by organic chemists for the characteristics of clean,green and environmental protection or other to C-H functionalization.It is important that the photochemistry and electrochemistry in organic synthesis is briefly introduced in this paper.The paper introduced the types of photosensitizer,catalytic properties,five quenching cycle mode and two reaction modes of one pool.At present,C-H functionalization is mainly studied from the perspective of energy and electron.Visible light induces C-H functionalization mainly through reduction quenching and related cycle path,and the quenching path through oxidation is inseparable from participating transition metal Ir or Ru.C-H functionalization is mainly through anodic oxidation path by current induced,rarely through cathodic reduction.Therefore,the paper put forward an organic photosensitizer PTH inducing C-H Functionalization via a mode of oxidative quenching by visible light and a path of cathodic reduction.The main research results are as follows:（1）Firstly,the paper reported that we developed a highly efficient method for synthesis photosensitizer of PTH,and reduced the production cost of it.Secondly,we mixed together the photosensitizer PTH and CBr₄ to successfully solve the scientific problems and challenges,which realized the PTH that could stabilize the excited state without high-energy ultraviolet light in acetonitrile solution and visible light irradiation.We realized a study of external oxidant free selective C5 bromination of8-aminoquinoline amides under ambient conditions in acetonitrile and under the blue light irradiating by the oxidation quenching type path,the overall yield is good.（2）In this paper,we developed a strategy of selective C5 bromination of8-aminoquinoline amides by electrochemical method in cathodic reduction type path.An oxidant free and mild cathodic reduction for the functionalization of C-H bond is reported,which is different from the traditional anodic oxidation.