The Synthesis, Characterization, Applications Of Bisperfluorobutylsulfonate Bisbutyltin In Organic Synthesis

Organotin compounds are being wildly used in organic synthetic reations as Lewis acid. Normally, their Lewis acidity is too mild to form carbon-carbon bond. Hence, the increase of the Lewis acidity of organic organotin compounds is of prime importance to expand the scope of their synthetic utility. One of the useful means for this purpose is to attach electron-withdrawing group(s) on tin.Perfluoroalky- lsulfonate is such an electron-withdrawing group. It's reported that trifluoromethy- lsulfonic tin can catalyze carbon-carbon bond-forming reactions effectively. However their hygroscopic nature did not allow us to fully characterize the structure of these compounds. And it's reported perfluorooctanesulfonate metal compounds are air-stable and water-stable compound. In this paper, we synthesize and characterize Bisperfluorobutylsulfonate Bisbutyltin compound. Furthermore,The present thesis involves applications of Bisperfluorobutylsulfonate Bisbutyltin in Organic Synthesis.The contents of the paper include five parts:1.Bisperfluorobutylsulfonate Bisbutyltin was synthesized using C4F9SO3Ag and Bu2SnCl2 at room temperature, the yield of which is up to 74.6%. The product was Characterized by 1H NMR and 19F NMR, and the stability of which was studied in air and water, as well as the solubility in organic solvent.2.Bisperfluorobutylsulfonate Bisbutyltin catalyzes Esterification reaction. aromatic Alcohol and Ac2O react at room temperature in short time. the reaction of long-fatty alcohol and Ac2O needs higher temperature by Bisperfluorobutylsulfonate Bisbutyltin as catalyst. The yield of the reaction is up to 90% .3.Bisperfluorobutylsulfonate Bisbutyltin catalyzes Friedel-Crafts reaction. Aromatic oxide and acetyl chloride were stirred for 3-12h at room temperature or in heating, Then the mixture was subjected to column chromatography on silica gel to afford the pure product. The yield of the reaction is up to 55% .4.Bisperfluorobutylsulfonate Bisbutyltin catalyzes Allylation reaction. Allyl compounds are important intermediate of Organic Synthesis.That aldehyde and re tetraallyltin react by Lewis acid as catalyst is the common way of carbon-carbon bond formation.in this .In this pater,the reaction of aromatic aldehydeand tetraallyltin by bisperfluorobutylsulfonate bisbutyltin as catalyst at room temperature in CH3CN form new carbon-carbon bond,then a series of unsaturated aromatic alcohol were synthesized, the good yield of which is up to 95%. Meanwhile the amount of the catalyst and the prime solvent were studied. 5.Bisperfluorobutylsulfonate Bisbutyltin catalyzes the Mukaiyama-Aldol reaction of aromatic aldehyde and trimethylsilane. A series of aromatic alcohol compounds were synthesized at room temperature. The products were easy separated from catalyst, and the yield of which is up to 90%.