| In the present development of chemical industry,it is an important research direction in green pharmaceuticals research to developefficient,highly selective,and environment-friendly organic synthetic methods.Cross-Dehydrogenation Coupling(CDC)reaction attracts much attention of scientific researchers who devote themselves to the formation of carbon-carbon bonds because of its high efficiency and high atomic economy.Besides,mechanochemistry is an interdisciplinary cross-field science which has unique advantages for green synthetic chemistry.In this disertation,CDC reactions under mechanical grinding conditions were studied,including the following three chapters:The first chapter mainly introduced the recent research of CDC reaction catalyzed by iron salts,and asymmetric CDC reactions under ball milling condition.In the second chapter,indole derivatives were prepared by CDC reaction under ball milling conditions.The reaction was carried out with 2-phenyl-3-arylmethylindole and malonic acid.Great effort was made to optimize the reaction conditions,including catalyts,oxidatant,grinding time and frequency.Then,the scope and mechanism of this methodology were investigated.Finally,we had built up a protocol for 2,3-disubstituted indole derivatives with the advantages of low cost catalyts,simple operation process,short reaction time and high efficiency.This method was further applied to the preparation of Streptindole and Nomofungin/Communesin B which were pharmaceutical intermediates and greatly simplified their synthetic procedures.In the third chapter,an asymmetric version of CDC reaction was introduced to prepare the indole derivatives through the introduction of organic chiral ligands.The reaction was optimized by screening chiral ligands,liquid grinding auxiliary,catalyts,grinding time and frequency.Then,the scope of this methodology was investigated,which finally gave the indole derivatives in medium yields with good enantioselectivity. |
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