One-pot Multi-component Synthesis Of Aromatic Amine Selenide With Inorganic Selenium As Raw Material

Selenium is a rare element necessary for the human body.It has a variety of important physiological functions,such as anti-cancer and improves immunity.Selenium-containing organic compounds are also an important class of organic compounds.There are very few organic selenium compounds in natural products,but there are some inorganic compounds containing selenium,such as elemental selenium and selenium dioxide.Inorganic selenium compounds cannot be directly absorbed and utilized by the human body.On the contrary,they have a certain toxic effect on the human body.Therefore,the conversion of inorganic selenium into organic selenium compounds with different structures through chemical synthesis is a popular research direction.There are often many electron-rich structure compounds in nature,such as aniline structure and imidazopyridine structure.These electron-rich compounds have the possibility to react with inorganic selenium compounds.The core of the problem is how to use inorganic selenides to react with these electron-rich compounds To build a C-Se bond.In this paper,KSeCN and Se powder are used as selenium sources,aniline compounds are used as substrates,aromatic iodine compounds or aromatic boric acid compounds are used as other substrates,and the three-component one-pot method is used to construct diaryls under relatively green and mild conditions.Amine selenide provides a new method for the synthesis of selenide in the future.In the second part of this paper,we used selenium dioxide as the source of selenium and aromatic amine compounds as substrates,without transition metal catalysis,in a three-step synthesis of ArSe-substituted aromatic amine structure,synthesis The method is novel,the conditions are mild and environmentally friendly,and a new idea for synthesizing organic selenium compounds using inorganic selenium is explored.The main experiment of this paper includes the following two aspects:One:Utilize the electron-rich nature of aromatic amine structure,use KSeCN or Se powder as selenium source,iodobenzene compounds or phenylboronic acid compounds as another reaction substrate,use copper salt as catalyst,and polar organic solvent as reaction solvent,A multi-component one-step synthesis of aryl selenide in a relatively mild reaction atmosphere,the two reactions developed have better functional group tolerance for substrates with different substituents?electron withdrawing and electron donating?,Therefore,all reactions have higher reaction yields.Two:On the basis of the previous experiment,using the electron-rich characteristics of aromatic amine structure and imidazopyridine structure,using selenium dioxide as the selenium source,phenylboronic acid compounds as another reaction substrate,using KI as the catalyst,DMSO As a reaction solvent,diaryl selenide was synthesized in a multi-component step without transition metals.The reaction has a wider tolerance of functional groups,and the yield of the resulting product is higher.The developed method has a relatively good novelty,and has a great enlightening effect on the subsequent reactions involving SeO₂ as a selenium source.In conclusion,three different methods of synthesizing organic selenides were reported in this paper using different inorganic selenium sources.The three methods all show a wide range of functional group adaptability,and all of them can obtain the required organic selenium compounds in good yield.The reaction conditions are mild,and the reagents used are cheap and easy to obtain,especially reported in the second part of the paper Reaction,the reaction does not require the participation of transition metals,and fully meets the requirements of green chemistry.The three methods provide a research idea for future selenium chemistry research.