Direct Palladium-catalyzed C-3 Alkynylation Of Indoles And Direct Acetoxylation And Etherification Of Anilides Using Organoiodine(III) Oxidant

Cross-coupling reaction is one the important reactions in organic chemistry. It finds wide applications in chemical engineering and medical syntheses. It is very limited for the traditional synthesis methods due to its specific catalyst and exigent parameter . To meet the requirement of the environmental and economical protection, the study on a high efficiency, low toxic, low price and environmental benign reaction system is of impending importance. Study the new cross-coupling reactions It is a new trend in organic chemistry and a challenging project in the green process for the chemical engineering.The paper contains three parts, one is Palladium-catalyzed direct C-3 alkynylation of indoles. One is Direct Acetoxylation and Etherification of Anilides using Phenyliodine Bis(trifluoroacetate) (PIFA). The third part is total synthesis of the model molecule of Sieboldine A and Alopecuridine.Firstly,the direct Palladium-catalyzed coupling reaction of indoles with alkynyl bromide has been developed to produce corresponding 3-alkynylindoles with high regioselectivity and in good to excellent yields under mild conditions.Secondly, the acetoxylation and etherification of anilides induced by organoiodine(III) oxidant were reported. In the presence of phenyliodine(III) bis(trifluoroacetate) (PIFA) and BF3·OEt2, the reaction of anilides with AcOH or MeOH at the room temperature gave the para-acetoxylated and para-methoxylated products with high regioselectivity in good to excellent yields.Thirdly, we studied the total synthesis of the model molecule of Sieboldine A and Alopecuridine. We introduced a new model molecule to study the key step of the total synthesis of Sieboldine A and Alopecuridine. And we experimented many different reactions under different conditions.