Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction Of Potassium 2-Pyridyl Trifluoroborate With Aryl (Heteroaryl) Halides

The thesis investigated the synthesis of potassium 2-pyridyltrifluoroborate and its application in Suzuki-Miyaura cross-coupling reaction.1. Synthesis of potassium 2-pyridyltrifluoroborate (Scheme 1).The potassium 2-pyridyltrifluoroborate with different substitution could be easily prepared from organohalides followed by lithium/halide exchange, boronation, hydrolysis, and in situ KHF2 treatment.2. The Suzuki-Miyaura cross-coupling reaction of potassium 2-pyridyltrifluoroborate with aryl (heteroaryl) halides.The Suzuki-Miyaura cross-coupling reaction of substituted potassium 2-pyridyltrifluoroborate with aryl (heteroaryl) halides was investigated. It was found that Suzuki-Miyaura cross-coupling reaction of potassium 2-pyridyltrifluoroborate with aryl (heteroaryl) halides, with Pd(OAc)2 (3 mol%) and SPhos (6 mol%), can produce moderate to good yields by using Na2CO3 as base, ethanol as solvent, this reaction system was found to be compatible with various functional groups such as amines, carbonyl, aminomethyl, etc (Scheme 2).