Electrosynthetic Reactions With Arylboronic Acids To Construct C-S/Se Bonds

Organo-selenium/sulfides are not only important components of many chemical products and natural compounds,but also important intermediates for organic synthesis.The incorporation of selenium/sulfur element into the structure of small drug molecules can remarkably change their properties including physical and chemical performances,enhance the interaction between the small drug molecule and the target protein to improve the efficacy.Therefore,the synthesis of compounds containing sulfide/selenide is a hot topic in synthetic chemistry.Since they are cheap,non-toxic,stable and easily available reagents,the transformation with arylboronic acids as substrates has been favored for a long time,significantly,the Suzuki coupling reaction with aryl boric acid was awarded Nobel Prize in Chemistry in 2010.It is noteworthy that the reaction sites are single and selective in deborylative functionalization of arylboronic acids.In recent years,it has been a green,economical and environmentally friendly method to achieve the desired transformation using current as the promoter.Thus,we hope to find a kind of stable and non-toxic selenium/sulfur-based source to construct C-S/Se bond with arylboronic acids as substrates using current as the promoter under green environmental conditions.The main contents of this thesis are the deborylative functionalization of arylboronic acids under electrochemical conditions,1)using KSeCN and TMSNCS as the selenium/thiocyanate source to establish deborylative seleno/thiocyanation of arylboronic acids;2)employing RSeSeR(R=Me,Ar)as the selenium-based source to realize deborylative selenolation of arylboronic acids.