The Synthesis And Application Of Fluorous Boronates Without Perfluorinated Solvents And Synthesis Of Fluorous Acohols And Fluorous Carboxylic Acids

By directly addressing the separation problems inherent in the synthesis of small organic molecules, fluorous techniques provide an array of powerful solutions that span the discipline of organic synthesis from large-scale chemical processes through traditional fine synthesis to modern chemical discovery by combinatorial methods. In recent years, a lot of fluorous catalysts, reagents and fluorous separation methods were successfully applied in organic synthesis. However, the research of fluorous chemistry is not sufficient compared with solid-phase synthesis. In this dissertation, fluorous technique without perfluorinated solvents is mainly discussed. Fluorous diol 4 has been designed and synthesized. Its application in organic synthesis also has been investigated in detail. Common fluorous building blocks have been synthesized through perfluoroalkyl iodide.Fluorous technique without perfluorinated solvents has been applied to organic boron chemistry for the first time. Fluorous diol 4 has been designed and synthesized, and a series of boronic acid were attached to 4 by esterification. All the formed fluorous boronates 5 underwent the Suzukicross-coupling reaction in good yields and the fluorous diol 4 was recycled in good yield. "Fluorous Molecules bearing one long perfluoroalkyl chain have bad solubility in organic solvents or fluorous solvents, however, raising temperature can remarkably improve their solubility in both phase." Act as this rule, the isolation of products was facilitated. The hydroboration of alkynes with fluorous borane (~FPBH) 10 has also been investigated.Fluorous alcohols and fluorous carboxylic acids are important synthesis precursors. Fluorous alcohols 13, 17 and fluorous carboxylic acids 14 were synthesized readily. The yields of the reactions were evidently increased by switching the solvents.