Novel Synthetic Methodology For 3,3,3-trifluoropropynyllithium And Its Application In Organic Synthesis

Synthesis of carbon-carbon triple bond,which is a bridge of various organic materials, has been applied to many fields. Synthetic methodologies of 3,3,3-trifluoropropargyl-containing compounds with superior performance raises additional concerns. Such methods usually started from 3,3,3-trifluoropropynyl lithium, magnesium, zinc reagent. Alkynylstannane, one of the branches in construction of carbon-carbon bond, is of great importance in synthetic chemistry.This thesis includes the following four areas:1. Summarized two kinds of cross-coupling reaction of organic tin compounds with organic electrophile, which is direct coupling reaction and carbonylation coupling reaction.2. The Stille reaction which mainly in the organic tin and halogenated hydrocarbons halogenated aromatic hydrocarbons, and carbonyl chloride was reviewed in detail. 3. Synthesis of 2,2-dichloro-1-trifluoromethylvinyl tosylate and its application in produce of3,3,3-trifluoropropynyllithium, which was reacted with 2 eq of n-butyl lithium. Furthermore, the application of 3,3,3-trifluoropropynyllithium with many kinds of electrophile was studied and corresponding 3,3,3-trifluoropropynyl-containing compounds were prepared via the installed method. All the structures were analyzed by 1H NMR,19F NMR,13C NMR,119Sn NMR,MS,IR and elemental analysis.4. Novel synthetic method for aryl trifluoromethyl alkynes from tributyl(3,3,3- trifluoropropynyl)stannane and aryl iodide catalyzed by palladium was constructed and its application was studied detailly. Meanwhile, aryl trifluoromethyl alkynes was synthesized from 3,3,3-trifluoropropynylzinc and aryl iodide catalyzed by palladium and their structures were confirmed by 1H NMR,19F NMR,13C NMR,119Sn NMR,MS,IR and elemental analysis.