Coupling Reaction Of Benzyl Alcohol Derivatives With Active Methylene Compounds Mediated By Fluoroalkanesulfonyl Fluoride

Perfluoroalkanesulfonyl fluoride(RfSO2f) is a new kind of excellent hydroxyl activating reagent. Based on this property, it has been successfully applied in the formation of C-X bond(such as C-O, C-N, C-S, C-F bonds) and in the total synthesis of some natural products. In consideration of the facts that this reagent can activate hydroxyl group thus producing a carbacation center, and the reaction of an active methylene compound with a base can generate an anion center, we imagined that RfSO2 F will induce the coupling reaction of an alcohol(resource of the carbocation) and an active methylene compound(resource of the anion) under alkaline conditions. The experimental results proved our hypothesis. We will report these result in this thesis. This methodology has the advantages of mild reaction condition,ease of handling and high yielding. The above research results will provide an alternate novel C-C bond formation methodology. The thesis contains the following two parts:1.The coupling reaction of C-C bond and the literatures of Perfluoroalkanesulfonyl fluoride- induced reactions were reviewed.2.The pefluoroalkanesulfonyl fluorides–induced coupling reaction of benzyl alcohol derivatives with active methylene compounds under alkaline condition was investigated in detail. Firstly, the reaction conditions were optimized. And secondly, the application scope of substrates was studied. Finally, a possible reaction mechanism was proposed to intercept the research results.