The Synthesis Of Fluorinated Phenylboronic Acids (Boroxins) And Its Application In The Carbon-Sulfur Coupling Reaction

This dissertation consisted of two parts. The first chapter is focused on the synthesis and application of fluorinated phenylboronic acids(boroxins). The second one is the application of fluorinated phenylboronic acids(boroxins) in the carbon-sulfur coupling reactions.In the first part, firstly, we simply outlined the synthesis of fluorinated phenylboronic acids(boroxins) and its applications in organic synthesis. Secondly, we gave a brief review on the traditional synthetic method of 3-fluorophenyl acid and improved a green route to prepare it from 1-bromo-3-fluorobenzene, via Grignard reaction, boronation, hydrolization, the yield of 85% was obtianed. This reaction is using 2-methyltetrahydrofuran as green solvent, friendly to environment,. The advantages of our present procedure are mild reaction condition, simple operation, economical, environment friendly, so it can be considered of good prospect for industrial application.In the second part, firstly, the research progress of C-S coupling reaction and synthesis of C-S bond formation were briefly reviewed. Secondly, we developed a novel C-S bond formation using boroxins and disulfides by cuprous iodide/1,10-phenanthroline, in DMSO/H2O(1:1), under oxygen atmosphere to give the corresponding fluorinated arylsulfides up 90% yields. The reaction conditions were investigated and aplausible mechanism for this reaction was proposed in the paper. Further studies on the application of pentafluorophenylboronic acid are now in progress.