Iodine-catalyzed One-pot Synthesis Of ?-ketoamides And Benzils

1,2-Dicarbonyl is an important structural and functional unit of many organic compounds. This dissertation describes two convenient methods towards the synthesis of ?-ketoamide and benzil compounds containing 1,2-dicarbonyl fragment. ?-Ketoamide plays an important role in biologically active substances and natural products which serve as useful substances in daily life. Although lots of effort has been made to construct ?-ketoamide, almost all of these methods suffer from some limitations, such as hazardous reagents, tedious steps to prepare active starting materials, harsh reaction conditions, and so on. To develop a general, mild, convenient, and environmentally benign method is clearly needed. A one-pot synthetic protocol of ?-ketoamides from aryl substituted alkene or alkyne using iodine as catalyst and tert-butyl hydroperoxide as oxidant is described in this dissertation. On the basis of synthesis of ?-ketoamide, a novel and efficient direct oxidative synthesis of benzils from acetophenone was also realized in the presence of iodine and DMSO under mild conditions. Compared with conventional synthetic methods, both protocols have the advantages of good atomic economy, mild reaction condition, high yielding, and avoiding using heavy metal catalyst, which has solved the drawbacks of harsh condition, poor availability of starting materials, and low yielding in previous ?-ketoamide and benzyl systhesis.