Study On Sn Mediated "One-Pot" Allylation And N-Heterocyclic Carbene Catalyzed Electrophilic Fluorination

Organotin reagent is one of the most important organic reagents used in theorganic synthesis. Among organotin reagents, allylstannanes have been widely used inorganic synthesis as stable and stereodefined reagents for C–C bond formation.However, with the development of green chemistry, allylstannanes also have somelimitations in organic synthesis. In this paper, tin metal promoted, involving in situformations of allyltin without any additive, one-pot reaction was firstly disclosed. Atthe same time, we preliminary explored electrophilic fluorination andtrifluoromethylation reaction catalyzed by N-heterocyclic carbenes.The thesis mainly consists of the following four parts:The first chapter: TheApplication ofAllylstannanes to in the Organic SynthesisThis chapter presents an overview of tremendous studies towards recentadvances in the application of allylstannanes to in the organic synthesis.(1)Mechanistic aspects of allylation of aldehydes with allylstannanes;(2) Allylstannanesas allylating reagents applied in the organic synthesis;(3) Activation of allylstannanesby transmetalation;(4) The application of allylstannanes to the asymmetric allylation.The second chapter: Studies on Sn Mediated One-Pot AllylationA convenient and facile synthesis of homoallylic amines was described in thischapter. The desired compounds were prepared by four-component allylation reactionof aldehydes, aromatic amines and allylic bromide reacted with tin powder in one potwithout any promoter or additive. The method has the advantages of being additivefree, highly efficient, bench friendly and environmentally benign.The third chapter: Studies on Sn Mediated One-Pot Allyl Substitution ReactionIn this chapter, we provided a new synthesis method of1,5-dienes by the reactionof1,3-diphenylallyl acetate, allylic bromide and tin powder. This process is a veryconvenient, high efficient, low cost and concise manipulation.The fourth chapter: Electrophilic Fluorination and TrifluoromethylationCatalyzed by N-heterocyclic carbenes. In this chapter, we preliminary explored electrophilic fluorination andtrifluoromethylation reaction catalyzed by N-heterocyclic carbenes.