| Oxindole derivatives are the most important heterocyclic skeletons in chemistry biology and medicine.These heterocyclic skeletons are widely found in pharmaceutical molecules and organic synthesis intermediates,also often used as a skeleton structure of synthesis of complex natural products,which are favored by chemists.Oxindole derivatives have a wide range of potential applications in biology,medicine and other fields.Therefore,the development of efficient strategies for the synthesis of oxindole derivatives has attracted extensive attention in the past few decades.Compared with many traditional methods to synthesize indole derivatives,these methods usually need to synthesize special reaction precursors,the reaction conditions are harsh,and the limitations in industrial application are relatively large.The transition metal catalyzed Heck carbonylation reaction developed in recent years is an efficient and simple synthesis method with simple operation and mild reaction conditions.In this paper,the reaction mechanisms and strategies of palladium-catalyzed enantioselective Heck cyclation and palladium-catalyzed asymmetric carbonylation were firstly summarized,and then the reaction of transition metal catalyzed carbonylation was reviewed.Based on these and previous work,a class of palladium-assisted enantioselective carbonylation of dominoes was designed and reported.At 100 ° C,the total pressure is one atmosphere and the ratio of carbon monoxide to argon is 1:6.Under the mixed atmosphere,palladium catalyzed Heck carbonylation reaction was carried out using N-arylacrylamide and arylboric acid compounds as substrates.Finally,a series of 3,3-disubstituted indole derivatives were synthesized by using the classical reaction Suzuki coupling to terminate the reaction.At 45℃,the chiral 3,3-disubstituted indole derivatives with 74% yield and 91%ee were obtained by the design of ligands.The reaction is simple and efficient,the raw material cost is low and easy to obtain,and the reaction has a very high range of substrate application and functional group compatibility,which can effectively improve the diversity of synthesis methods of 3,3-disubstrated indole derivatives. |
