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A Study On Two Reaction Of Carbon-sulfur Bonds Based On Difunctionalization Of Alkynes

Posted on:2022-12-15Degree:MasterType:Thesis
Country:ChinaCandidate:H R JinFull Text:PDF
GTID:2481306779983179Subject:Electric Power Industry
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Alkynes are important molecular building blocks in organic synthesis.Because they contain unsaturated carbon-carbon triple bonds,complex molecules were preparation from alkynes via electrophilic addition and radical addition reactions.In recent years,the difunctionalization of alkynes for construction of a series of bioactive molecules and functional materials has been reported successively.Organosulfur compounds are important targeted molecules in medicinal and biological chemistry,as well as important intermediates in organic synthesis.Therefore,the synthesis of such compounds is very important in theory studies and organic applications.Among the numerous C–S bond construction reactions,the one-step construction of organosulfides using difunctionalization of alkynes has attracted great interest from chemists due to its atom-and step-economy.Today,the development of more efficient,green,transition metal-free methods for construction of C–S bonds is becoming important targets.In this paper,a mild and efficient synthetic method for the construction of carbon-sulfur bonds was discolsed through the difunctionalization reaction of alkynes,and?-thiocyanate vinyl sulfone and thiol-substituted phenanthrenes were selectively synthesized.The main contents are as follows:1.A novel and efficient method for the synthesis of ?-thiocyanate vinyl sulfone has been achieved from readily available arylsulfinic acids,KSCN and alkynes through direct difunctionalization of carbon-carbon triple bonds,providing a range of structurally diverse products in good to excellent yields under mild conditions.2.BF3·Et2O-promoted tandem cyclization of alkynes and N-arylthio succinimides was achieved for synthesis of thiol-substituted phenanthrenes with good to excellent yields.This sequential process is conducted at room temperature,and it provides a novel,mild,simple and efficient method for the synthesis of thiol-substituted phenanthrenes under metal-free conditions.
Keywords/Search Tags:difunctionalization of alkynes, arylsulfinic acids, phenanthrene rings, C-S bonds
PDF Full Text Request
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