Palladium-catalyzed Reaction Of Alkynes With Arylation Reagents

Catalytic reaction of carbon-carbon triple bonds is an important method for constructing complex molecules from relatively simple precursors. For example, Sonogashira coupling and hydroarylation of alkynes have been intensively studied. This thesis will develop air-stable palladium-catalyzed Sonogashira coupling reaction and acetic acid-free hydroarylation of alkynes with arylboronic acids. Then one-pot reaction of Sonogashira coupling and hydroarylation was developed for the synthesis of trisubstituted olefins. This thesis including four chapters is as follows.1) The hydroarylation and Sonogashira coupling of alkynes was reviewed, then our research idea was proposed.2) An efficient hydroarylation was developed without a common additional acetic acid.3) The development of air-stable palladium-catalyzed Sonogashira coupling. A facility method to prepare disubstituted acetylenes has been developed.4) A one-pot reaction is highly effective for the high regioselective synthesis of trisubstituted olefins via an air-stable sequential Sonogashira and hydroarylation reaction of readily available aliphatic or aromatic terminal alkynes.The remarkable advantages of the above reactions are mild reaction conditions, simple operation, high yields. Especially, the use of the multifunctional catalyst for one-pot reactions generates less waste and also obviates the tedious separation and purification of the intermediate products as well as inert gas protection. This approach opens up an easy access to trisubstituted olefins.