Coupling Reaction of Organoboronic Acids with Chloropyrimidines and Trichlorotriazine

• 作 者: 谭久青 常建华 邓敏智
• 机 构: Department of Chemistry,Northwest University,Xi'an,Shaanxi 710069,China,Department of Chemistry,Nort
• 出 处: Chinese Journal of Chemistry
• 发表日期: 2004年09期
• 关键词: triazine pyrimidine substituted convenient symmetrical chloro steric starting pr

Pd-catalyzed cross-coupling reactions of chloropyrimidines with alkenylboronic acids readily proceed to give the corresponding alkenylpyrimidines in high to excellent yields. The coupling reaction of 2,4-dichloropyrimidine or 2,4,6-trichloropyrimidine with one equivalent of alkenylboronic acid occurred more easily on 4-position than on 2-position, which implied that the reaction is highly regioselective. The reaction is stereospecific since the configu-ration of C=C remained intact. The preliminary study on the cross-coupling reactions of 2,4,6-trichlorotriazine with one equivalent of arylboronic acids showed that the reactions afforded the monosubstituted triazines in moder-ate yields. The effect of steric hindrance of the substitutents on the reactions was found.

Pd-catalyzed cross-coupling reactions of chloropyrimidines with alkenylboronic acids are favorable to give the corresponding alkenylpyrimidines in high to excellent yields. The coupling reaction of 2,4-dichloropyrimidine or 2,4,6-trichloropyrimidine with one equivalent of alkenylboronic acid event more easily on 4-position than on 2-position, which implied that the reaction is highly regioselective. The reaction is stereospecific since the configu-ration of C = C unchanged intact. The preliminary study on the cross-coupling reactions of 2,4, The effect of steric hindrance of the substitutents on the reactions was found.