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Direct Tosyloxylation of Anilides Using Phenyliodine Bis (Trifluoroacetate) and Palladium-catalyzed Cyclization/Coupling Reaction of Indoles

Author: LiuHuan
Tutor: GuYongHong
School: University of Science and Technology of China
Course: Organic Chemistry
Keywords: anilide hypervalent iodine tosyloxylation indole palladium-catalyzed oxidative coupling
CLC: O643.32
Type: Master's thesis
Year: 2011
Downloads: 57
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Abstract


As an important class of organic compounds, aromatic compounds have been widely used in natural products and pharmaceuticals. In particular acetyl aniline and indoles derivatives exhibit a wide range of biological activities and spread widely in the nature, the development of efficient methods for the syntheses of arylindoles has attracted great research interest in the last several decades. Selective and efficient oxygenation of aromatic compounds is one of the most challenging reactions in organic synthesis. Recently, oxidation by using hypervalent iodine compounds has been rapidly developed. hypervalent iodine compounds as metal-free reagents has received much attention for their low toxicity mild reaction conditions, easy handling and special reactivity in oxidation reactions. Palladium-catalyzed cross-coupling reaction direct arylation has been a major objective in organic synthesis chemistry. Especially the Palladium-catalyzed tandem reaction caused extensive research interest, for its high efficiency, short reaction steps, rapid synthesis of complex organic products.The thesis contains two parts, the first one is Direct tosyloxylation of anilides using phenyliodine bis(trifluoroacetate) (PIFA). The second one is palladium- catalyzed cyclization/coupling reaction of indoles with 1-Bromoethynyl -2-methoxy-benzene.Firstly, the direct tosyloxylation of anilides has been developed. In the presence of phenyliodine bis(trifluoroacetate) (PIFA), the reaction gave para- tosyloxylated products with excellent yields. The advantage of these reactions are widely used as an inexpensive, safe, and environmentally benign oxidant, easy handling and fastly reactive, only about half hour, the reactions complete.Secondly palladium-catalyzed coupling reaction of indoles with 1-Bromoethynyl -2-methoxy-benzene was described in this part. The reaction realized one pot sequentive coupling/cyclization to provide complexed benzofuran derivatives in good yield. The benefits of this reaction include mild reaction condition, without nitrogen protection. This reaction give a new way for the synthesis of complexed benzofuran compounds.

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CLC: > Mathematical sciences and chemical > Chemistry > Physical Chemistry ( theoretical chemistry ),chemical physics > Chemical kinetics,catalysis > Catalytic > Catalytic reaction
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