Electrochemically Enabled Carbohydroxylation Of Alkenes And C-H Phosphorylation Of Arenes And C-H Alkylation Of Heteroarenes

C-H functionalization is an effective method to forge carbon chain skeleton and introduce various functional groups.Organic electrochemistry,as a sustainable synthesis method,eschewing the need for stoichiometric oxidants or reductants,which provides efficient strategies for the construction of a variety of important structures.In this paper,1,2-difunctionalization of alkenes,C-H phosphorylation of arenes and photoelectrochemical C-H alkylation were reported by electrochemical oxidation.In the first part,1,2-difunctionalization of alkenes,which adds one functional group to each carbon of double bond,provides a straightforward strategy for organic synthesis.Although extensive range of studies in this area were reported,only a few works have explored the synthesis of functionalized alkenes via the direct addition of an alkynyl or alkenyl group.In contrast,the more challenging three-component intermolecular 1,2-difunctionalization of alkenes remain rare.Herein we reported the electrochemically enabled regio-and chemoselective carbohydroxylation of alkenes with alkynyl or alkenyl group.Under the electrochemical conditions,the organotrifluoroborates containing negative charge was probably absorbed on the anode surface which detected by Raman spectroscopy.Consequently,relatively high concentration of the organotrifluoroborates ensures the highly regio-and chemoselectivities of intermolecular 1,2-difunctionalization of alkenes.In the second part,organophosphorus compounds have wide application in medicinal chemistry,materials sciences and biology.Compared with well-established transition metal-catalyzed method,direct C-H phosphorylation of arenes is more attractive owing to the obviation of substrate prefunctionalization.The mild conditions of the electrosynthesis in continuous flow and the high reactivity of the P-radical cations make C-H phosphorylation readily accessible to arenes of diverse electronic properties,especially compatible with deficient arenes and complex natural products.The electrochemical method was characterized by broad scope and the continuous production of 55 grams of the phosphonate products.In the third part,Minisci-type reactions,which furnish net C-H alkylation in heteroarenes by addition of carbon-centered radicals to electron-deficient heterocycles,has been intensively studied over the past few decades.Organoboronic acids and their derivatives are among the most prominent molecules used in organic chemistry.Herein,we reported a novelty photoelectrochemical C-H alkylation of heteroarenes by using 1°,2° and 3° organoboron reagents especially with boronic acid pinacol ester.The photoelectrochemical method has broad scope and compatible with complex natural products.