Studies On The Formation Of C-F Bond And P-F Bond Catalyzed By Transition Metal

In the past decade, research on transition metal-catalyzed C-H bond reaction has become a promising project. Transition metal-catalyzed C-H bond activation to build the C-X bond（X = C, N, O, etc.） is the most simple and efficient synthetic method with atom economy in organic synthesis. Thus, the research of the basic rule of the C-H bond activation and cleavage has the important academic significance and great practical value.Organophosphorus compounds widely present in the nucleotides and drugs, and played an irreplaceable role. Organic phosphorus compounds containing P-F bond is very important, it is often used as a molecular probe or some enzyme inhibitors, so the research on the construction of P-F bond is also a very important academic and practical value.This thesis includes the following:In first chapter, studies on transition-metal-catalyzed carbene or carbenoid intermediates that undergo C–H bond insertion reactions.In second chapter, studies on transition-metal-catalyzed fluorination reaction are reviewed.In third chapter, Ruthenium-catalyed intramolecular cyclization and fluorination to form 3-fluorooxindoles. A is simple, efficient and environmentally-friendly method avoids to use oxidizing agent, alkali and other additives. Ruthenium-catalyzed α-diazoacetamides decomposed to form ruthenium-carbene, and then cyclization and fluorination to form the corresponding fluorination products.In four chapter, Copper-promoted oxidative-fluorinating reaction of arylphosphine under mild condition. A simple efficient method for the synthesis of phosphoric fluoride via oxidative coupling between hydrophosphine oxide and NaF with DDQ under mild reaction conditions. The process exhibits great functional group tolerance. The addition reaction of diphenylphosphine oxide and DDQ catalyzed by copper bromide to form phenol phosphinate as an intermediate A, then NaF as the fluorinating reagent reacts with intermediate A through a SN₂ pathway to give the fluorinated product.