Research On The Formation Of C-CN Bond Based On The New Cyanide Sources

Nitriles are useful intermediates in organic synthesis and play a crucial role inmany fields as they can be easily converted into a variety of functional groups such asacids and amines. They also have a widespread application in the fields of pesticide,dyes and pharmaceuticals. So the study of cyanation is of great value not only inacademic research but also in its wide application in various fields. However, most ofcyanations use metal cyanide as cyanide sources which always cause metal waste,harsh reaction conditions, environmental pollution, and other issues. To solve theseproblems, exploring new cyanide sources have attracted more and more attention.Acetonitrile is a common organic solvent. It is non-toxic, environment-friendlyand readily available without the need of complicated pre-processing. However, theC-CN bond in acetonitrile is difficult to break. So the research on using it as cyanidesource is rare in report.In this thesis, we report the investigation of the transition-metal catalyzedcyanation of arenediazonium tetrafluoroborates using acetonitrile as the cyanidesource. We found that palladium chloride and the silver oxide could broke C-CN bondand make the reaction proceed smoothly. We have optimized the reaction condition bychanging the reaction temperature, catalyst, oxidizing agent, and reaction time. Thescope of substrates were also investigated as well. Acetonitrile show some advantageswhen compared to other cyanide sources. This method not only provides a new wayfor the synthesis of benzene nitrile compounds, but also provides a new idea thatacetonitrile can be widely used in cyanations.The cyanations using NCTS and PbfCN as cyanide sources were alsoinvestigated. NCTS and PbfCN are stable and easy to operate. They are newnon-metallic cyanide sources. We have explored the cyanation of anisole, benzoicacid, and1,3-dicarbonyl compound. In the case of benzoic acid was used as thesubstrate, a new cyanide was obtained.