Research On Carbonyl Olefination And Iron-Catalyzed Coupling Reaction Of Terminal Alkyne

Carbon-carbon double bonds and 1,3-diyne are both the invaluable structures in organic synthesis, so it benefits to develop a convenient and efficient method to construct these structures.The thesis consists of the following two sections.1. Research on the reaction of Carbonyl Olefination. The widely available carbonyl compounds react with Grignard reagents to give the corresponding olefins in good to excellent yields. And a range of conjugated dienes, terminal olefins ,multisubstituted-alkenes, homoallylic bromides and conjugated enynes could be readily obtained in the mild conditions by changing the structure of carbonyl compounds or Grignard reagents. The yields of both electron-donating and electron-withdrawing groups be employed in benzene rings are good to excellent. Moreover, thiophene and furan heterocycles participate efficiently in the reaction. Especially, E-olefins could be obtained as the predominant products by the reaction of aldehydes with Grignard reagents in high stereoselectivity. We have appended the work of probing the mechanism for this olefination process and given the possible mechanism.2. Research on the reaction of iron-catalyzed coupling reaction of terminal alkyne. The structure of 1,3–diyne exists in many organic intermediates and natural medicines. We have attempted to synthesis the 1,3–diyne via the Glaser coupling reaction by iron–catalyzed., and expanded the application of iron reagents in organic synthesis .