Suzuki Cross-coupling Reaction. Chlorinated Electron Deficient With Aza-aromatic Ring Compounds And Organic Boric Acid

The thesis comprises two parts: Part IThe cross-coupling reactions of 2,4,6-trichlorotriazine with one equivalent of arylboronic acids were investigated in preliminary, it was found that the reactions can couple smoothly to give the monosubstituted triazines in moderate to good yields. The effect of the hindrance of the substitutents on the reactions appeared. Under the same conditions, the alkenylboronic acid and the cyclopropyl boronic acid were also studied. The alkenylboronic acid with 2,4,6-trichlorotriazine can couple to give the corresponding alkenylsubstituted triazine, however, using cyclopropyl boronic acid as partener, the reaction didn't take place at all (under the optimum conditions we choosed).Part IIUnder appropriate conditions, Pd-catalyzed cross-coupling reactions of various chloropyrimidines with alkenylboronic acids can readily proceed to give the corresponding alkenylpyrimidines in high to excellent yields. In the coupling of 2,4-dichloropyrimidine and 2,4,6-trichloropyrimidine with one equivalent of alkenylboronic acid, the reaction occurred on 4-position prior to on 2-position. The reaction is high regioselective and stereospeciflc. This is a new convenient method for preparing various stereodefined alkenylpyrimidines. The coupling reactions of cyclopropylboronic acids with pyrimidine were examed, it was very pity that the reaction didn't occur(under the same conditions), and the work would be further studied.