Studies On Synthesis Of 1,2-/1,4-dicarbonyl Compound

This dissertation reviewed the synthesis methods for dicarbonyl compounds in recent years,focusing on the synthesis of alpha-,beta-,gamma-dicarbonyl compounds and their application.Then we studied on various reaction types and developed several novel routines to access dicarbonyl compounds by using carbon-carbon bond cleavage reaction and oxidative coupling reaction.The main research contents of this dissertation are as follows:1.We report a novel Selectfluor-mediated simultaneous cleavage of C-O and C-C bonds in?,?-epoxy ketones leading to 1,2-diketone compounds in moderate to good yields under transition-metal-free conditions.The highest yield of the reaction was 85%,and the method has the advantages of mild reaction conditions,high yields and broad scope of substrates.2.We report a novel Cu-catalyzed intramolecular oxidative coupling reaction in o-alkynyl-acetophenone leading to 1,4-naphthoquinone compounds.The Cu I/Cu(OTf)₂combined system is the catalyst of this method.DMSO plays a dual role in the reaction,namely acting as oxidant and solvent.The highest yield of the reaction was 75%,and the method has the advantages of using cheap catalyst,simple operation and broad scope of substrates.3.We report a novel transition-metal-free aerobic oxidative cyclization-homocoupling reaction in(o-acetyl)-1,2-diones leading to1,4-naphthoquinone dimers.The highest yield of the reaction was 95%,and the method has the advantages of mild reaction condition,simple operation and good substrate compatibility.